NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	886.46
Volume:	848.159
LogP:	2.28
LogD:	0.841
LogS:	-3.234
# Rotatable Bonds:	7
TPSA:	276.14
# H-Bond Aceptor:	18
# H-Bond Donor:	10
# Rings:	9
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.141
Synthetic Accessibility Score:	6.826
Fsp3:	0.955
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:	-6.211
MDCK Permeability:	0.00029114665812812746
Pgp-inhibitor:	0.003
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.794
20% Bioavailability (F20%):	0.101
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	72.41327667236328%
Volume Distribution (VD):	-0.068
Pgp-substrate:	9.91315746307373%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.917
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.286
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	0.563
Half-life (T1/2):	0.727

ADMET: Toxicity

hERG Blockers:	0.809
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.449
Rat Oral Acute Toxicity:	0.245
Maximum Recommended Daily Dose:	0.254
Skin Sensitization:	0.94
Carcinogencity:	0.159
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC477028

Natural Product ID:	NPC477028
*Common Name:**	Spiroconazolea
IUPAC Name:	(2R,3R,4R,5R,6R)-6-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-[(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-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxyoxane-2,3,4,5-tetrol
Synonyms:
Standard InCHIKey:	OFNAYKGAZRKBJB-FXVFWNRRSA-N
Standard InCHI:	InChI=1S/C44H70O18/c1-18-8-13-43(55-17-18)20(3)44(54)27(62-43)15-25-23-7-6-21-14-22(9-11-41(21,4)24(23)10-12-42(25,44)5)57-40-36(60-39-34(52)31(49)32(50)37(53)61-39)35(29(47)26(16-45)58-40)59-38-33(51)30(48)28(46)19(2)56-38/h6,18-20,22-40,45-54H,7-17H2,1-5H3/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-/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)CO)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)O)O)O)O)C)C)O)C)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49799045
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
NPO20181	Dracaena arborea	Species	Asparagaceae	Eukaryota	bark	Yaound, village of Bangoua, near Bangangt	2007-APR	PMID[20553003]
NPO20181	Dracaena arborea	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	=	1670	nM	PMID[20553003]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	2040	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 NPC477028 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	309
0.1-0.2	2186
0.2-0.3	7799
0.3-0.4	14009
0.4-0.5	7892
0.5-0.6	5496
0.6-0.7	2886
0.7-0.8	1385
0.8-0.85	434
0.85-0.9	161
0.9-0.95	67
0.95-1	73

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477032
1.0	High Similarity	NPC124677
0.9806	High Similarity	NPC13193
0.9804	High Similarity	NPC46190
0.9804	High Similarity	NPC150372
0.9804	High Similarity	NPC6806
0.9804	High Similarity	NPC309278
0.9804	High Similarity	NPC475333
0.9804	High Similarity	NPC470433
0.9804	High Similarity	NPC73243
0.9804	High Similarity	NPC102016
0.9804	High Similarity	NPC40440
0.9804	High Similarity	NPC475550
0.9804	High Similarity	NPC95051
0.9804	High Similarity	NPC249265
0.9804	High Similarity	NPC208383
0.9804	High Similarity	NPC300557
0.9804	High Similarity	NPC218571
0.9804	High Similarity	NPC22779
0.9804	High Similarity	NPC244086
0.9804	High Similarity	NPC224098
0.9804	High Similarity	NPC171073
0.9804	High Similarity	NPC42482
0.9804	High Similarity	NPC232054
0.9804	High Similarity	NPC248746
0.9804	High Similarity	NPC194207
0.9804	High Similarity	NPC477809
0.9804	High Similarity	NPC84956
0.9714	High Similarity	NPC167183
0.9714	High Similarity	NPC32707
0.9712	High Similarity	NPC254255
0.9709	High Similarity	NPC477811
0.9709	High Similarity	NPC269297
0.9709	High Similarity	NPC222202
0.9709	High Similarity	NPC87998
0.9709	High Similarity	NPC224314
0.9709	High Similarity	NPC23808
0.9706	High Similarity	NPC98696
0.9623	High Similarity	NPC477031
0.9619	High Similarity	NPC79900
0.9615	High Similarity	NPC197231
0.9615	High Similarity	NPC475247
0.9615	High Similarity	NPC476547
0.9615	High Similarity	NPC294129
0.9608	High Similarity	NPC283829
0.9608	High Similarity	NPC113044
0.9608	High Similarity	NPC14704
0.9608	High Similarity	NPC94272
0.9608	High Similarity	NPC230507
0.9608	High Similarity	NPC470432
0.9608	High Similarity	NPC305423
0.9608	High Similarity	NPC161676
0.9528	High Similarity	NPC477810
0.9524	High Similarity	NPC244431
0.9524	High Similarity	NPC31896
0.9524	High Similarity	NPC263359
0.9524	High Similarity	NPC32361
0.9524	High Similarity	NPC19888
0.9524	High Similarity	NPC210569
0.9524	High Similarity	NPC42171
0.9519	High Similarity	NPC247037
0.951	High Similarity	NPC474569
0.951	High Similarity	NPC181845
0.9434	High Similarity	NPC469347
0.9434	High Similarity	NPC469348
0.9423	High Similarity	NPC475670
0.9423	High Similarity	NPC306131
0.9423	High Similarity	NPC477026
0.9423	High Similarity	NPC70204
0.9423	High Similarity	NPC477027
0.9346	High Similarity	NPC477808
0.9346	High Similarity	NPC11548
0.934	High Similarity	NPC308140
0.9333	High Similarity	NPC141433
0.9327	High Similarity	NPC476538
0.9327	High Similarity	NPC476540
0.9327	High Similarity	NPC476539
0.9327	High Similarity	NPC476541
0.932	High Similarity	NPC309448
0.932	High Similarity	NPC26798
0.9259	High Similarity	NPC63609
0.9259	High Similarity	NPC477029
0.9259	High Similarity	NPC477030
0.9252	High Similarity	NPC476546
0.9252	High Similarity	NPC476693
0.9245	High Similarity	NPC470748
0.9238	High Similarity	NPC302057
0.9231	High Similarity	NPC226642
0.9231	High Similarity	NPC190395
0.9174	High Similarity	NPC477807
0.9167	High Similarity	NPC208832
0.9159	High Similarity	NPC112274
0.9143	High Similarity	NPC220427
0.9135	High Similarity	NPC473476
0.9135	High Similarity	NPC242748
0.9135	High Similarity	NPC473923
0.9074	High Similarity	NPC307642
0.9074	High Similarity	NPC51154
0.9074	High Similarity	NPC476671
0.9065	High Similarity	NPC13190
0.9057	High Similarity	NPC476835
0.9048	High Similarity	NPC63368
0.9048	High Similarity	NPC208650
0.9048	High Similarity	NPC14946
0.9038	High Similarity	NPC470885
0.9038	High Similarity	NPC221562
0.9038	High Similarity	NPC187400
0.9029	High Similarity	NPC272015
0.9009	High Similarity	NPC195560
0.9009	High Similarity	NPC229962
0.9	High Similarity	NPC20979
0.8962	High Similarity	NPC6931
0.8962	High Similarity	NPC295980
0.8962	High Similarity	NPC180183
0.8962	High Similarity	NPC246124
0.8962	High Similarity	NPC159005
0.8952	High Similarity	NPC152584
0.8952	High Similarity	NPC127801
0.8952	High Similarity	NPC69737
0.8952	High Similarity	NPC208594
0.8952	High Similarity	NPC194842
0.8952	High Similarity	NPC160816
0.8952	High Similarity	NPC269627
0.8952	High Similarity	NPC208477
0.8942	High Similarity	NPC475701
0.8938	High Similarity	NPC43842
0.8929	High Similarity	NPC198325
0.8929	High Similarity	NPC207243
0.8929	High Similarity	NPC50689
0.8929	High Similarity	NPC233391
0.8919	High Similarity	NPC475357
0.8919	High Similarity	NPC10366
0.8919	High Similarity	NPC476692
0.8919	High Similarity	NPC476691
0.8909	High Similarity	NPC148965
0.8868	High Similarity	NPC181467
0.8868	High Similarity	NPC473469
0.886	High Similarity	NPC202261
0.886	High Similarity	NPC295133
0.886	High Similarity	NPC257207
0.886	High Similarity	NPC106589
0.8857	High Similarity	NPC474464
0.885	High Similarity	NPC249553
0.885	High Similarity	NPC182900
0.885	High Similarity	NPC476544
0.885	High Similarity	NPC476543
0.885	High Similarity	NPC476545
0.8839	High Similarity	NPC473633
0.8839	High Similarity	NPC476085
0.8835	High Similarity	NPC282669
0.8829	High Similarity	NPC476690
0.8829	High Similarity	NPC100048
0.8824	High Similarity	NPC473890
0.8824	High Similarity	NPC243728
0.8785	High Similarity	NPC7213
0.8785	High Similarity	NPC125324
0.8785	High Similarity	NPC128123
0.8785	High Similarity	NPC49032
0.8785	High Similarity	NPC51172
0.8774	High Similarity	NPC474015
0.8772	High Similarity	NPC15918
0.8772	High Similarity	NPC305771
0.8772	High Similarity	NPC94072
0.8772	High Similarity	NPC169816
0.8762	High Similarity	NPC213190
0.8762	High Similarity	NPC131479
0.8762	High Similarity	NPC157659
0.8762	High Similarity	NPC31907
0.8762	High Similarity	NPC245280
0.8762	High Similarity	NPC189852
0.8762	High Similarity	NPC286969
0.8762	High Similarity	NPC114874
0.8762	High Similarity	NPC155010
0.8762	High Similarity	NPC472252
0.8762	High Similarity	NPC16520
0.8762	High Similarity	NPC8039
0.8762	High Similarity	NPC211879
0.8762	High Similarity	NPC120123
0.8762	High Similarity	NPC473020
0.8761	High Similarity	NPC475187
0.8761	High Similarity	NPC473566
0.8761	High Similarity	NPC475358
0.875	High Similarity	NPC475403
0.875	High Similarity	NPC160888
0.8739	High Similarity	NPC146652
0.8739	High Similarity	NPC279638
0.8738	High Similarity	NPC158088
0.8727	High Similarity	NPC144068
0.8716	High Similarity	NPC114188
0.8716	High Similarity	NPC92710
0.8704	High Similarity	NPC250089
0.8704	High Similarity	NPC14630
0.8704	High Similarity	NPC151134
0.8704	High Similarity	NPC157530
0.8696	High Similarity	NPC160084
0.8696	High Similarity	NPC256983
0.8679	High Similarity	NPC165033
0.8679	High Similarity	NPC471111
0.8679	High Similarity	NPC475365
0.8679	High Similarity	NPC273879

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 NPC477028 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	2353
0.2-0.3	4425
0.3-0.4	1393
0.4-0.5	370
0.5-0.6	255
0.6-0.7	73
0.7-0.8	20
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8276	Intermediate Similarity	NPD8377	Approved
0.8276	Intermediate Similarity	NPD8294	Approved
0.8205	Intermediate Similarity	NPD8380	Approved
0.8205	Intermediate Similarity	NPD8379	Approved
0.8205	Intermediate Similarity	NPD8335	Approved
0.8205	Intermediate Similarity	NPD8296	Approved
0.8205	Intermediate Similarity	NPD8378	Approved
0.8205	Intermediate Similarity	NPD8033	Approved
0.8077	Intermediate Similarity	NPD8171	Discontinued
0.8065	Intermediate Similarity	NPD8450	Suspended
0.7984	Intermediate Similarity	NPD8449	Approved
0.7857	Intermediate Similarity	NPD6412	Phase 2
0.7797	Intermediate Similarity	NPD7327	Approved
0.7797	Intermediate Similarity	NPD7328	Approved
0.7759	Intermediate Similarity	NPD8133	Approved
0.7731	Intermediate Similarity	NPD7516	Approved
0.7603	Intermediate Similarity	NPD7503	Approved
0.7398	Intermediate Similarity	NPD6370	Approved
0.7381	Intermediate Similarity	NPD7736	Approved
0.7368	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7507	Approved
0.7302	Intermediate Similarity	NPD8293	Discontinued
0.7236	Intermediate Similarity	NPD6054	Approved
0.7236	Intermediate Similarity	NPD6059	Approved
0.7188	Intermediate Similarity	NPD7319	Approved
0.7119	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD8328	Phase 3
0.704	Intermediate Similarity	NPD6015	Approved
0.704	Intermediate Similarity	NPD6016	Approved
0.7008	Intermediate Similarity	NPD7492	Approved
0.6992	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5988	Approved
0.6953	Remote Similarity	NPD6616	Approved
0.6944	Remote Similarity	NPD7524	Approved
0.6929	Remote Similarity	NPD6067	Discontinued
0.6923	Remote Similarity	NPD6928	Phase 2
0.6905	Remote Similarity	NPD8515	Approved
0.6905	Remote Similarity	NPD8516	Approved
0.6905	Remote Similarity	NPD8517	Approved
0.6899	Remote Similarity	NPD7078	Approved
0.6891	Remote Similarity	NPD6686	Approved
0.6863	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8513	Phase 3
0.6765	Remote Similarity	NPD7339	Approved
0.6765	Remote Similarity	NPD6942	Approved
0.6762	Remote Similarity	NPD7525	Registered
0.6729	Remote Similarity	NPD6695	Phase 3
0.6721	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6033	Approved
0.6693	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD7750	Discontinued
0.6587	Remote Similarity	NPD6009	Approved
0.6538	Remote Similarity	NPD6933	Approved
0.6509	Remote Similarity	NPD7645	Phase 2
0.6505	Remote Similarity	NPD4784	Approved
0.6505	Remote Similarity	NPD4785	Approved
0.6503	Remote Similarity	NPD7625	Phase 1
0.6493	Remote Similarity	NPD5956	Approved
0.6491	Remote Similarity	NPD6399	Phase 3
0.648	Remote Similarity	NPD4632	Approved
0.6475	Remote Similarity	NPD7320	Approved
0.6471	Remote Similarity	NPD4243	Approved
0.6449	Remote Similarity	NPD6931	Approved
0.6449	Remote Similarity	NPD6930	Phase 2
0.6446	Remote Similarity	NPD6008	Approved
0.6446	Remote Similarity	NPD6675	Approved
0.6446	Remote Similarity	NPD7128	Approved
0.6446	Remote Similarity	NPD6402	Approved
0.6446	Remote Similarity	NPD5739	Approved
0.6423	Remote Similarity	NPD6372	Approved
0.6423	Remote Similarity	NPD6373	Approved
0.641	Remote Similarity	NPD6083	Phase 2
0.641	Remote Similarity	NPD6084	Phase 2
0.6371	Remote Similarity	NPD4634	Approved
0.6364	Remote Similarity	NPD4786	Approved
0.6356	Remote Similarity	NPD7638	Approved
0.6355	Remote Similarity	NPD6929	Approved
0.6346	Remote Similarity	NPD6926	Approved
0.6346	Remote Similarity	NPD6924	Approved
0.6341	Remote Similarity	NPD6881	Approved
0.6341	Remote Similarity	NPD6899	Approved
0.6321	Remote Similarity	NPD6932	Approved
0.632	Remote Similarity	NPD8130	Phase 1
0.632	Remote Similarity	NPD6649	Approved
0.632	Remote Similarity	NPD6650	Approved
0.6303	Remote Similarity	NPD7639	Approved
0.6303	Remote Similarity	NPD7640	Approved
0.6296	Remote Similarity	NPD4748	Discontinued
0.6271	Remote Similarity	NPD4755	Approved
0.6261	Remote Similarity	NPD7087	Discontinued
0.626	Remote Similarity	NPD5701	Approved
0.626	Remote Similarity	NPD5697	Approved
0.624	Remote Similarity	NPD7102	Approved
0.624	Remote Similarity	NPD7290	Approved
0.624	Remote Similarity	NPD6883	Approved
0.6239	Remote Similarity	NPD7991	Discontinued
0.6228	Remote Similarity	NPD4753	Phase 2
0.6228	Remote Similarity	NPD6051	Approved
0.6207	Remote Similarity	NPD4202	Approved
0.6204	Remote Similarity	NPD6683	Phase 2
0.6202	Remote Similarity	NPD7115	Discovery
0.619	Remote Similarity	NPD6847	Approved
0.619	Remote Similarity	NPD6869	Approved
0.619	Remote Similarity	NPD6617	Approved
0.6182	Remote Similarity	NPD3667	Approved
0.6168	Remote Similarity	NPD6925	Approved
0.6168	Remote Similarity	NPD5776	Phase 2
0.6167	Remote Similarity	NPD5286	Approved
0.6167	Remote Similarity	NPD4700	Approved
0.6167	Remote Similarity	NPD4696	Approved
0.6167	Remote Similarity	NPD5285	Approved
0.6165	Remote Similarity	NPD7604	Phase 2
0.6161	Remote Similarity	NPD6893	Approved
0.616	Remote Similarity	NPD6014	Approved
0.616	Remote Similarity	NPD6013	Approved
0.616	Remote Similarity	NPD6012	Approved
0.6147	Remote Similarity	NPD7514	Phase 3
0.6142	Remote Similarity	NPD6053	Discontinued
0.6136	Remote Similarity	NPD5983	Phase 2
0.6132	Remote Similarity	NPD4190	Phase 3
0.6132	Remote Similarity	NPD5275	Approved
0.6116	Remote Similarity	NPD4159	Approved
0.6111	Remote Similarity	NPD7145	Approved
0.6102	Remote Similarity	NPD5695	Phase 3
0.6083	Remote Similarity	NPD5696	Approved
0.608	Remote Similarity	NPD6011	Approved
0.6074	Remote Similarity	NPD6336	Discontinued
0.6071	Remote Similarity	NPD3133	Approved
0.6071	Remote Similarity	NPD3665	Phase 1
0.6071	Remote Similarity	NPD3666	Approved
0.6066	Remote Similarity	NPD4633	Approved
0.6066	Remote Similarity	NPD5224	Approved
0.6066	Remote Similarity	NPD5225	Approved
0.6066	Remote Similarity	NPD5226	Approved
0.6066	Remote Similarity	NPD5211	Phase 2
0.6063	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD4195	Approved
0.6048	Remote Similarity	NPD4768	Approved
0.6048	Remote Similarity	NPD4767	Approved
0.6017	Remote Similarity	NPD7748	Approved
0.6016	Remote Similarity	NPD5174	Approved
0.6016	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD6903	Approved
0.6	Remote Similarity	NPD7509	Discontinued
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD7151	Approved
0.6	Remote Similarity	NPD7332	Phase 2
0.6	Remote Similarity	NPD7152	Approved
0.6	Remote Similarity	NPD7150	Approved
0.6	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD8336	Approved
0.5985	Remote Similarity	NPD8337	Approved
0.5984	Remote Similarity	NPD5223	Approved
0.5983	Remote Similarity	NPD8034	Phase 2
0.5983	Remote Similarity	NPD8035	Phase 2
0.5983	Remote Similarity	NPD7637	Suspended
0.5968	Remote Similarity	NPD5141	Approved
0.5966	Remote Similarity	NPD5210	Approved
0.5966	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD4629	Approved
0.5965	Remote Similarity	NPD6684	Approved
0.5965	Remote Similarity	NPD7334	Approved
0.5965	Remote Similarity	NPD7521	Approved
0.5965	Remote Similarity	NPD7146	Approved
0.5965	Remote Similarity	NPD6409	Approved
0.5965	Remote Similarity	NPD5330	Approved
0.5962	Remote Similarity	NPD6923	Approved
0.5962	Remote Similarity	NPD6922	Approved
0.5952	Remote Similarity	NPD4730	Approved
0.5952	Remote Similarity	NPD4729	Approved
0.595	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.595	Remote Similarity	NPD4225	Approved
0.5948	Remote Similarity	NPD5328	Approved
0.5946	Remote Similarity	NPD6902	Approved
0.5946	Remote Similarity	NPD6898	Phase 1
0.5912	Remote Similarity	NPD8074	Phase 3
0.5906	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD7144	Approved
0.5905	Remote Similarity	NPD7143	Approved
0.5897	Remote Similarity	NPD3168	Discontinued
0.5893	Remote Similarity	NPD4221	Approved
0.5893	Remote Similarity	NPD4223	Phase 3
0.5888	Remote Similarity	NPD1811	Approved
0.5888	Remote Similarity	NPD1810	Approved
0.5887	Remote Similarity	NPD4754	Approved
0.5878	Remote Similarity	NPD6274	Approved
0.5877	Remote Similarity	NPD5329	Approved
0.5873	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD7101	Approved
0.5865	Remote Similarity	NPD7100	Approved
0.5865	Remote Similarity	NPD4522	Approved
0.5859	Remote Similarity	NPD5247	Approved
0.5859	Remote Similarity	NPD5251	Approved
0.5859	Remote Similarity	NPD5250	Approved
0.5859	Remote Similarity	NPD5249	Phase 3
0.5859	Remote Similarity	NPD5248	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