NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1016.48
Volume:	958.607
LogP:	1.072
LogD:	0.761
LogS:	-3.512
# Rotatable Bonds:	8
TPSA:	335.06
# H-Bond Aceptor:	22
# H-Bond Donor:	12
# Rings:	10
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.109
Synthetic Accessibility Score:	7.41
Fsp3:	0.918
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:	-6.352
MDCK Permeability:	0.0002507041790522635
Pgp-inhibitor:	0.02
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.993
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.169
Plasma Protein Binding (PPB):	48.285240173339844%
Volume Distribution (VD):	0.037
Pgp-substrate:	35.19701385498047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.13
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	0.065
Half-life (T1/2):	0.757

ADMET: Toxicity

hERG Blockers:	0.535
Human Hepatotoxicity (H-HT):	0.232
Drug-inuced Liver Injury (DILI):	0.592
AMES Toxicity:	0.124
Rat Oral Acute Toxicity:	0.294
Maximum Recommended Daily Dose:	0.799
Skin Sensitization:	0.7
Carcinogencity:	0.357
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC477030

Natural Product ID:	NPC477030
*Common Name:**	(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-2-[(1S,2S,3'S,4S,4'S,6R,7S,8R,9S,12S,13R,14R,16R)-3',16-dihydroxy-7,9,13-trimethyl-5'-methylidene-4'-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-14-yl]oxy-5-hydroxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-4-yl]oxy-6-methyloxane-3,4,5-triol
IUPAC Name:	(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-2-[(1S,2S,3'S,4S,4'S,6R,7S,8R,9S,12S,13R,14R,16R)-3',16-dihydroxy-7,9,13-trimethyl-5'-methylidene-4'-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-14-yl]oxy-5-hydroxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-4-yl]oxy-6-methyloxane-3,4,5-triol
Synonyms:	Deistelianoside B
Standard InCHIKey:	WBBFDXFFYOWQNF-CTASHREFSA-N
Standard InCHI:	InChI=1S/C49H76O22/c1-17-14-64-49(42(61)39(17)68-43-36(58)33(55)26(51)15-62-43)18(2)30-28(71-49)13-25-23-8-7-21-11-22(50)12-29(48(21,6)24(23)9-10-47(25,30)5)67-46-41(70-44-37(59)34(56)27(52)16-63-44)40(32(54)20(4)66-46)69-45-38(60)35(57)31(53)19(3)65-45/h7,18-20,22-46,50-61H,1,8-16H2,2-6H3/t18-,19-,20+,22+,23+,24-,25-,26-,27+,28-,29+,30-,31-,32-,33-,34-,35+,36+,37+,38+,39-,40-,41+,42-,43-,44-,45-,46-,47-,48-,49+/m0/s1
SMILES:	C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4([C@@H](C[C@@H](C5)O)O[C@H]6[C@@H]([C@H]([C@H]([C@H](O6)C)O)O[C@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)C)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)C)C)O[C@@]19[C@H]([C@H](C(=C)CO9)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49799042
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	=	70730	nM	PMID[20553003]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	21250	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 NPC477030 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	317
0.1-0.2	2111
0.2-0.3	6317
0.3-0.4	13504
0.4-0.5	9312
0.5-0.6	5909
0.6-0.7	2993
0.7-0.8	1450
0.8-0.85	434
0.85-0.9	212
0.9-0.95	79
0.95-1	59

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477029
0.9906	High Similarity	NPC11548
0.9717	High Similarity	NPC42171
0.9717	High Similarity	NPC112274
0.9636	High Similarity	NPC207243
0.9636	High Similarity	NPC198325
0.9636	High Similarity	NPC233391
0.9626	High Similarity	NPC51154
0.9623	High Similarity	NPC13190
0.9623	High Similarity	NPC475247
0.9623	High Similarity	NPC294129
0.9545	High Similarity	NPC229962
0.9545	High Similarity	NPC195560
0.9528	High Similarity	NPC222202
0.9528	High Similarity	NPC23808
0.9528	High Similarity	NPC477811
0.9528	High Similarity	NPC269297
0.9528	High Similarity	NPC87998
0.9528	High Similarity	NPC224314
0.9459	High Similarity	NPC50689
0.945	High Similarity	NPC148965
0.9439	High Similarity	NPC13193
0.9434	High Similarity	NPC470433
0.9434	High Similarity	NPC309278
0.9434	High Similarity	NPC306131
0.9434	High Similarity	NPC477026
0.9434	High Similarity	NPC46190
0.9434	High Similarity	NPC244086
0.9434	High Similarity	NPC70204
0.9434	High Similarity	NPC477027
0.9434	High Similarity	NPC6806
0.9434	High Similarity	NPC194207
0.9434	High Similarity	NPC232054
0.9434	High Similarity	NPC248746
0.9434	High Similarity	NPC84956
0.9434	High Similarity	NPC475670
0.9434	High Similarity	NPC218571
0.9434	High Similarity	NPC477809
0.9434	High Similarity	NPC150372
0.9434	High Similarity	NPC475333
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	NPC95051
0.9434	High Similarity	NPC300557
0.9434	High Similarity	NPC249265
0.9434	High Similarity	NPC475550
0.9381	High Similarity	NPC202261
0.9381	High Similarity	NPC106589
0.9369	High Similarity	NPC473633
0.9369	High Similarity	NPC476085
0.9364	High Similarity	NPC477807
0.9364	High Similarity	NPC20979
0.9358	High Similarity	NPC477810
0.9352	High Similarity	NPC31896
0.9352	High Similarity	NPC263359
0.9352	High Similarity	NPC32361
0.9352	High Similarity	NPC210569
0.9352	High Similarity	NPC244431
0.934	High Similarity	NPC476538
0.934	High Similarity	NPC476541
0.934	High Similarity	NPC476540
0.934	High Similarity	NPC98696
0.934	High Similarity	NPC476539
0.9292	High Similarity	NPC43842
0.9279	High Similarity	NPC160888
0.9279	High Similarity	NPC475403
0.9273	High Similarity	NPC63609
0.9266	High Similarity	NPC79900
0.9266	High Similarity	NPC469347
0.9266	High Similarity	NPC469348
0.9259	High Similarity	NPC477028
0.9259	High Similarity	NPC124677
0.9259	High Similarity	NPC477032
0.9259	High Similarity	NPC476547
0.9245	High Similarity	NPC14704
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	NPC113044
0.9211	High Similarity	NPC295133
0.9211	High Similarity	NPC257207
0.9182	High Similarity	NPC167183
0.9182	High Similarity	NPC32707
0.9182	High Similarity	NPC477808
0.9174	High Similarity	NPC308140
0.9167	High Similarity	NPC247037
0.9167	High Similarity	NPC141433
0.9151	High Similarity	NPC473923
0.9151	High Similarity	NPC473476
0.9151	High Similarity	NPC181845
0.9107	High Similarity	NPC10366
0.9083	High Similarity	NPC197231
0.9074	High Similarity	NPC14630
0.9074	High Similarity	NPC157530
0.9074	High Similarity	NPC250089
0.9074	High Similarity	NPC42482
0.9074	High Similarity	NPC302057
0.9074	High Similarity	NPC40440
0.9065	High Similarity	NPC226642
0.9018	High Similarity	NPC100048
0.9018	High Similarity	NPC476690
0.9009	High Similarity	NPC208832
0.9	High Similarity	NPC254255
0.9	High Similarity	NPC19888
0.8991	High Similarity	NPC470867
0.8981	High Similarity	NPC125324
0.8981	High Similarity	NPC49032
0.8981	High Similarity	NPC51172
0.8972	High Similarity	NPC309448
0.8972	High Similarity	NPC242748
0.8938	High Similarity	NPC475357
0.8929	High Similarity	NPC477031
0.8919	High Similarity	NPC476671
0.8919	High Similarity	NPC307642
0.8919	High Similarity	NPC476693
0.8919	High Similarity	NPC476546
0.8899	High Similarity	NPC151134
0.8889	High Similarity	NPC190395
0.8889	High Similarity	NPC473469
0.8879	High Similarity	NPC93352
0.8818	High Similarity	NPC170974
0.8818	High Similarity	NPC191439
0.8818	High Similarity	NPC103627
0.8807	High Similarity	NPC6931
0.8807	High Similarity	NPC159005
0.8807	High Similarity	NPC220427
0.8796	High Similarity	NPC474569
0.8783	High Similarity	NPC473566
0.8783	High Similarity	NPC475358
0.8774	High Similarity	NPC176406
0.8739	High Similarity	NPC470748
0.8727	High Similarity	NPC473328
0.8727	High Similarity	NPC28844
0.8727	High Similarity	NPC476835
0.8727	High Similarity	NPC128133
0.8727	High Similarity	NPC473318
0.8718	High Similarity	NPC308262
0.8718	High Similarity	NPC117445
0.8718	High Similarity	NPC208193
0.8716	High Similarity	NPC54619
0.8716	High Similarity	NPC208650
0.8716	High Similarity	NPC63368
0.8716	High Similarity	NPC33053
0.8716	High Similarity	NPC14946
0.8704	High Similarity	NPC221562
0.8704	High Similarity	NPC187400
0.8704	High Similarity	NPC470885
0.8692	High Similarity	NPC272015
0.8661	High Similarity	NPC231797
0.8661	High Similarity	NPC216595
0.8661	High Similarity	NPC473567
0.8649	High Similarity	NPC65155
0.8636	High Similarity	NPC476513
0.8636	High Similarity	NPC180183
0.8636	High Similarity	NPC295980
0.8636	High Similarity	NPC246124
0.8636	High Similarity	NPC7213
0.8632	High Similarity	NPC74259
0.8632	High Similarity	NPC15918
0.8632	High Similarity	NPC474423
0.8632	High Similarity	NPC305771
0.8632	High Similarity	NPC169816
0.8632	High Similarity	NPC94072
0.8624	High Similarity	NPC269627
0.8624	High Similarity	NPC26798
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
0.8609	High Similarity	NPC476691
0.8609	High Similarity	NPC476692
0.8596	High Similarity	NPC146652
0.8584	High Similarity	NPC144068
0.8571	High Similarity	NPC208189
0.8571	High Similarity	NPC114188
0.8571	High Similarity	NPC473021
0.8571	High Similarity	NPC472987
0.8571	High Similarity	NPC92710
0.8571	High Similarity	NPC65034
0.8559	High Similarity	NPC256983
0.8547	High Similarity	NPC474908
0.8547	High Similarity	NPC475419
0.8547	High Similarity	NPC314535
0.8547	High Similarity	NPC476544
0.8547	High Similarity	NPC249553
0.8547	High Similarity	NPC120390
0.8547	High Similarity	NPC173555
0.8547	High Similarity	NPC476543
0.8547	High Similarity	NPC182900
0.8547	High Similarity	NPC476545

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 NPC477030 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	2238
0.2-0.3	4235
0.3-0.4	1630
0.4-0.5	434
0.5-0.6	271
0.6-0.7	56
0.7-0.8	12
0.8-0.85	7
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8547	High Similarity	NPD8296	Approved
0.8547	High Similarity	NPD8378	Approved
0.8547	High Similarity	NPD8380	Approved
0.8547	High Similarity	NPD8379	Approved
0.8547	High Similarity	NPD8335	Approved
0.8462	Intermediate Similarity	NPD8377	Approved
0.8462	Intermediate Similarity	NPD8294	Approved
0.839	Intermediate Similarity	NPD8033	Approved
0.8136	Intermediate Similarity	NPD7327	Approved
0.8136	Intermediate Similarity	NPD7328	Approved
0.8067	Intermediate Similarity	NPD7516	Approved
0.7812	Intermediate Similarity	NPD8450	Suspended
0.7797	Intermediate Similarity	NPD8133	Approved
0.7787	Intermediate Similarity	NPD7503	Approved
0.7778	Intermediate Similarity	NPD8171	Discontinued
0.7734	Intermediate Similarity	NPD8449	Approved
0.7586	Intermediate Similarity	NPD6412	Phase 2
0.754	Intermediate Similarity	NPD7507	Approved
0.75	Intermediate Similarity	NPD7319	Approved
0.7119	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD8515	Approved
0.7087	Intermediate Similarity	NPD8517	Approved
0.7087	Intermediate Similarity	NPD8516	Approved
0.7083	Intermediate Similarity	NPD6686	Approved
0.7031	Intermediate Similarity	NPD6370	Approved
0.7025	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD7736	Approved
0.6977	Remote Similarity	NPD8328	Phase 3
0.6953	Remote Similarity	NPD8513	Phase 3
0.6947	Remote Similarity	NPD8293	Discontinued
0.6911	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6059	Approved
0.6875	Remote Similarity	NPD6054	Approved
0.6847	Remote Similarity	NPD7524	Approved
0.6727	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6067	Discontinued
0.6695	Remote Similarity	NPD7638	Approved
0.6692	Remote Similarity	NPD6016	Approved
0.6692	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6928	Phase 2
0.6667	Remote Similarity	NPD7625	Phase 1
0.6641	Remote Similarity	NPD5988	Approved
0.6639	Remote Similarity	NPD7640	Approved
0.6639	Remote Similarity	NPD7639	Approved
0.6636	Remote Similarity	NPD6695	Phase 3
0.6617	Remote Similarity	NPD6616	Approved
0.6604	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7078	Approved
0.6549	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7750	Discontinued
0.6514	Remote Similarity	NPD7525	Registered
0.6509	Remote Similarity	NPD6942	Approved
0.6509	Remote Similarity	NPD7339	Approved
0.6457	Remote Similarity	NPD6882	Approved
0.6457	Remote Similarity	NPD8297	Approved
0.6446	Remote Similarity	NPD4159	Approved
0.6422	Remote Similarity	NPD6929	Approved
0.6422	Remote Similarity	NPD7645	Phase 2
0.6397	Remote Similarity	NPD6033	Approved
0.6385	Remote Similarity	NPD6009	Approved
0.6385	Remote Similarity	NPD7115	Discovery
0.6364	Remote Similarity	NPD6930	Phase 2
0.6364	Remote Similarity	NPD6931	Approved
0.6364	Remote Similarity	NPD6319	Approved
0.6293	Remote Similarity	NPD6051	Approved
0.6281	Remote Similarity	NPD4225	Approved
0.6279	Remote Similarity	NPD4632	Approved
0.6271	Remote Similarity	NPD6399	Phase 3
0.627	Remote Similarity	NPD7320	Approved
0.624	Remote Similarity	NPD5739	Approved
0.624	Remote Similarity	NPD6402	Approved
0.624	Remote Similarity	NPD6675	Approved
0.624	Remote Similarity	NPD6008	Approved
0.624	Remote Similarity	NPD7128	Approved
0.6239	Remote Similarity	NPD6925	Approved
0.6239	Remote Similarity	NPD5776	Phase 2
0.622	Remote Similarity	NPD6373	Approved
0.622	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6372	Approved
0.6202	Remote Similarity	NPD6053	Discontinued
0.6186	Remote Similarity	NPD7087	Discontinued
0.6182	Remote Similarity	NPD7145	Approved
0.6147	Remote Similarity	NPD6933	Approved
0.6142	Remote Similarity	NPD6881	Approved
0.6142	Remote Similarity	NPD6899	Approved
0.614	Remote Similarity	NPD4786	Approved
0.6129	Remote Similarity	NPD7632	Discontinued
0.6124	Remote Similarity	NPD6649	Approved
0.6124	Remote Similarity	NPD8130	Phase 1
0.6124	Remote Similarity	NPD6650	Approved
0.6111	Remote Similarity	NPD4785	Approved
0.6111	Remote Similarity	NPD4784	Approved
0.6091	Remote Similarity	NPD6932	Approved
0.6087	Remote Similarity	NPD8074	Phase 3
0.6087	Remote Similarity	NPD6893	Approved
0.6075	Remote Similarity	NPD4243	Approved
0.6071	Remote Similarity	NPD7514	Phase 3
0.6071	Remote Similarity	NPD5956	Approved
0.6066	Remote Similarity	NPD4755	Approved
0.6066	Remote Similarity	NPD6084	Phase 2
0.6066	Remote Similarity	NPD6083	Phase 2
0.6063	Remote Similarity	NPD5701	Approved
0.6063	Remote Similarity	NPD5697	Approved
0.605	Remote Similarity	NPD7637	Suspended
0.6048	Remote Similarity	NPD5344	Discontinued
0.6047	Remote Similarity	NPD4634	Approved
0.6047	Remote Similarity	NPD7290	Approved
0.6047	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD6883	Approved
0.6047	Remote Similarity	NPD7102	Approved
0.6033	Remote Similarity	NPD7991	Discontinued
0.6018	Remote Similarity	NPD6902	Approved
0.6016	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD6847	Approved
0.5985	Remote Similarity	NPD7604	Phase 2
0.5984	Remote Similarity	NPD6640	Phase 3
0.5982	Remote Similarity	NPD6683	Phase 2
0.5969	Remote Similarity	NPD6013	Approved
0.5969	Remote Similarity	NPD6014	Approved
0.5969	Remote Similarity	NPD6012	Approved
0.5968	Remote Similarity	NPD5286	Approved
0.5968	Remote Similarity	NPD4696	Approved
0.5968	Remote Similarity	NPD4700	Approved
0.5968	Remote Similarity	NPD5285	Approved
0.5965	Remote Similarity	NPD3667	Approved
0.5963	Remote Similarity	NPD6924	Approved
0.5963	Remote Similarity	NPD6926	Approved
0.5956	Remote Similarity	NPD5983	Phase 2
0.595	Remote Similarity	NPD7748	Approved
0.5938	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7902	Approved
0.5929	Remote Similarity	NPD7332	Phase 2
0.5929	Remote Similarity	NPD4748	Discontinued
0.5917	Remote Similarity	NPD8034	Phase 2
0.5917	Remote Similarity	NPD8035	Phase 2
0.5912	Remote Similarity	NPD5125	Phase 3
0.5912	Remote Similarity	NPD5126	Approved
0.5906	Remote Similarity	NPD5141	Approved
0.5899	Remote Similarity	NPD6336	Discontinued
0.5891	Remote Similarity	NPD6011	Approved
0.5882	Remote Similarity	NPD4753	Phase 2
0.5882	Remote Similarity	NPD5328	Approved
0.5878	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6898	Phase 1
0.5873	Remote Similarity	NPD5225	Approved
0.5873	Remote Similarity	NPD4633	Approved
0.5873	Remote Similarity	NPD5226	Approved
0.5873	Remote Similarity	NPD5224	Approved
0.5862	Remote Similarity	NPD3133	Approved
0.5862	Remote Similarity	NPD3666	Approved
0.5862	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD3665	Phase 1
0.5859	Remote Similarity	NPD4768	Approved
0.5859	Remote Similarity	NPD4767	Approved
0.5843	Remote Similarity	NPD7799	Discontinued
0.5833	Remote Similarity	NPD6698	Approved
0.5833	Remote Similarity	NPD3168	Discontinued
0.5833	Remote Similarity	NPD46	Approved
0.5833	Remote Similarity	NPD7838	Discovery
0.5827	Remote Similarity	NPD5174	Approved
0.5827	Remote Similarity	NPD5175	Approved
0.5816	Remote Similarity	NPD8336	Approved
0.5816	Remote Similarity	NPD8337	Approved
0.5814	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD6903	Approved
0.5794	Remote Similarity	NPD5223	Approved
0.5785	Remote Similarity	NPD7515	Phase 2
0.5785	Remote Similarity	NPD6079	Approved
0.578	Remote Similarity	NPD7152	Approved
0.578	Remote Similarity	NPD7150	Approved
0.578	Remote Similarity	NPD7151	Approved
0.5772	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD5695	Phase 3
0.5769	Remote Similarity	NPD4729	Approved
0.5769	Remote Similarity	NPD4730	Approved
0.5766	Remote Similarity	NPD5275	Approved
0.5766	Remote Similarity	NPD7741	Discontinued
0.5766	Remote Similarity	NPD4190	Phase 3
0.5763	Remote Similarity	NPD7146	Approved
0.5763	Remote Similarity	NPD3618	Phase 1
0.5763	Remote Similarity	NPD7334	Approved
0.5763	Remote Similarity	NPD6684	Approved
0.5763	Remote Similarity	NPD6409	Approved
0.5763	Remote Similarity	NPD7521	Approved
0.5763	Remote Similarity	NPD5330	Approved
0.576	Remote Similarity	NPD5696	Approved
0.5741	Remote Similarity	NPD6923	Approved
0.5741	Remote Similarity	NPD6922	Approved
0.5714	Remote Similarity	NPD4251	Approved
0.5714	Remote Similarity	NPD6430	Approved
0.5714	Remote Similarity	NPD6648	Approved
0.5714	Remote Similarity	NPD6429	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