NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	470.23
Volume:	490.319
LogP:	3.448
LogD:	2.656
LogS:	-4.203
# Rotatable Bonds:	5
TPSA:	103.04
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.472
Synthetic Accessibility Score:	5.388
Fsp3:	0.519
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.819
MDCK Permeability:	1.484006588725606e-05
Pgp-inhibitor:	0.978
Pgp-substrate:	0.514
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.102
30% Bioavailability (F30%):	0.156

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.668
Plasma Protein Binding (PPB):	96.00849151611328%
Volume Distribution (VD):	2.173
Pgp-substrate:	6.303694248199463%

ADMET: Metabolism

CYP1A2-inhibitor:	0.288
CYP1A2-substrate:	0.471
CYP2C19-inhibitor:	0.725
CYP2C19-substrate:	0.606
CYP2C9-inhibitor:	0.877
CYP2C9-substrate:	0.401
CYP2D6-inhibitor:	0.198
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.811
CYP3A4-substrate:	0.547

ADMET: Excretion

Clearance (CL):	7.773
Half-life (T1/2):	0.807

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.958
Drug-inuced Liver Injury (DILI):	0.87
AMES Toxicity:	0.49
Rat Oral Acute Toxicity:	0.797
Maximum Recommended Daily Dose:	0.871
Skin Sensitization:	0.829
Carcinogencity:	0.864
Eye Corrosion:	0.017
Eye Irritation:	0.047
Respiratory Toxicity:	0.586

Download Data

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

Natural Product: NPC476595

Natural Product ID:	NPC476595
*Common Name:**	(3R,5S,6S,7R,9R,10R,13R,16R,17R)-16-[(2R,3R,4R,5S)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(1S)-1-hydroxy-2-methoxyethyl]oxolan-2-yl]oxy-3-hydroxy-5-[(1S)-1-hydroxy-2-methoxyethyl]oxolan-2-yl]oxy-17-[(2R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6,7-triol
IUPAC Name:	(3R,5S,6S,7R,9R,10R,13R,16R,17R)-16-[(2R,3R,4R,5S)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(1S)-1-hydroxy-2-methoxyethyl]oxolan-2-yl]oxy-3-hydroxy-5-[(1S)-1-hydroxy-2-methoxyethyl]oxolan-2-yl]oxy-17-[(2R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6,7-triol
Synonyms:
Standard InCHIKey:	QQJQWKXILNHTPD-YHTDQUDTSA-N
Standard InCHI:	InChI=1S/C43H74O14/c1-9-22(20(2)3)11-10-21(4)31-29(17-25-30-24(13-15-43(25,31)6)42(5)14-12-23(44)16-26(42)32(47)33(30)48)54-41-36(51)39(38(56-41)28(46)19-53-8)57-40-35(50)34(49)37(55-40)27(45)18-52-7/h20-24,26-29,31-41,44-51H,9-19H2,1-8H3/t21-,22?,23-,24+,26-,27+,28+,29-,31+,32+,33-,34-,35-,36-,37+,38+,39-,40+,41-,42-,43+/m1/s1
SMILES:	CCC(CC[C@@H](C)[C@H]1[C@@H](CC2=C3[C@H](CC[C@]12C)[C@]4(CC[C@H](C[C@@H]4[C@@H]([C@@H]3O)O)O)C)O[C@H]5[C@@H]([C@H]([C@@H](O5)[C@H](COC)O)O[C@H]6[C@@H]([C@H]([C@@H](O6)[C@H](COC)O)O)O)O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	46886869
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

*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
NPO19207	Anthenea chinensis	Species	n.a.	n.a.	n.a.	at a depth of 2-20 m, Sanya Bay in the South China Sea	2007-OCT	PMID[20184290]
NPO19207	Anthenea chinensis	Species	n.a.	n.a.	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	3

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	2800	nM	PMID[20184290]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	4900	nM	PMID[20184290]
NPT2	Others	Unspecified		IC50	>	24500	nM	PMID[20184290]

☑ 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 NPC476595 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	280
0.1-0.2	2092
0.2-0.3	6270
0.3-0.4	13831
0.4-0.5	9242
0.5-0.6	6208
0.6-0.7	3667
0.7-0.8	1068
0.8-0.85	34
0.85-0.9	1
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476593
0.9796	High Similarity	NPC476594
0.9694	High Similarity	NPC476592
0.8641	High Similarity	NPC75608
0.8585	High Similarity	NPC141433
0.8476	Intermediate Similarity	NPC226642
0.8411	Intermediate Similarity	NPC247037
0.8396	Intermediate Similarity	NPC476539
0.8396	Intermediate Similarity	NPC476541
0.8396	Intermediate Similarity	NPC476538
0.8396	Intermediate Similarity	NPC476540
0.8381	Intermediate Similarity	NPC472900
0.8381	Intermediate Similarity	NPC472898
0.8381	Intermediate Similarity	NPC26798
0.8381	Intermediate Similarity	NPC242748
0.8381	Intermediate Similarity	NPC181845
0.8381	Intermediate Similarity	NPC472899
0.8365	Intermediate Similarity	NPC473198
0.835	Intermediate Similarity	NPC470434
0.8349	Intermediate Similarity	NPC307642
0.8349	Intermediate Similarity	NPC51154
0.8349	Intermediate Similarity	NPC476693
0.8349	Intermediate Similarity	NPC144068
0.8333	Intermediate Similarity	NPC275865
0.8333	Intermediate Similarity	NPC216260
0.8333	Intermediate Similarity	NPC197231
0.8333	Intermediate Similarity	NPC13190
0.8333	Intermediate Similarity	NPC5358
0.8333	Intermediate Similarity	NPC476547
0.8333	Intermediate Similarity	NPC309493
0.8318	Intermediate Similarity	NPC250089
0.8318	Intermediate Similarity	NPC476835
0.8318	Intermediate Similarity	NPC475670
0.8318	Intermediate Similarity	NPC477026
0.8318	Intermediate Similarity	NPC477027
0.8318	Intermediate Similarity	NPC14630
0.8318	Intermediate Similarity	NPC70204
0.8318	Intermediate Similarity	NPC306131
0.8318	Intermediate Similarity	NPC157530
0.8302	Intermediate Similarity	NPC283829
0.8302	Intermediate Similarity	NPC470432
0.8302	Intermediate Similarity	NPC230507
0.8302	Intermediate Similarity	NPC113044
0.8302	Intermediate Similarity	NPC161676
0.8302	Intermediate Similarity	NPC14704
0.8302	Intermediate Similarity	NPC305423
0.8288	Intermediate Similarity	NPC476690
0.8288	Intermediate Similarity	NPC100048
0.8286	Intermediate Similarity	NPC475365
0.8286	Intermediate Similarity	NPC93352
0.8257	Intermediate Similarity	NPC473567
0.8257	Intermediate Similarity	NPC19888
0.8257	Intermediate Similarity	NPC216595
0.8257	Intermediate Similarity	NPC31896
0.8257	Intermediate Similarity	NPC254255
0.8257	Intermediate Similarity	NPC244431
0.8257	Intermediate Similarity	NPC112274
0.8257	Intermediate Similarity	NPC32361
0.8257	Intermediate Similarity	NPC210569
0.8257	Intermediate Similarity	NPC263359
0.8252	Intermediate Similarity	NPC91497
0.8252	Intermediate Similarity	NPC469942
0.8252	Intermediate Similarity	NPC64348
0.8241	Intermediate Similarity	NPC170974
0.8241	Intermediate Similarity	NPC103627
0.8241	Intermediate Similarity	NPC191439
0.8241	Intermediate Similarity	NPC65155
0.8235	Intermediate Similarity	NPC240372
0.8224	Intermediate Similarity	NPC98696
0.8214	Intermediate Similarity	NPC10366
0.8208	Intermediate Similarity	NPC473476
0.8208	Intermediate Similarity	NPC473923
0.819	Intermediate Similarity	NPC475701
0.819	Intermediate Similarity	NPC213190
0.8182	Intermediate Similarity	NPC79900
0.8165	Intermediate Similarity	NPC294129
0.8165	Intermediate Similarity	NPC475247
0.8148	Intermediate Similarity	NPC475550
0.8148	Intermediate Similarity	NPC22779
0.8148	Intermediate Similarity	NPC232054
0.8148	Intermediate Similarity	NPC171073
0.8148	Intermediate Similarity	NPC28844
0.8148	Intermediate Similarity	NPC470433
0.8148	Intermediate Similarity	NPC42482
0.8148	Intermediate Similarity	NPC224098
0.8148	Intermediate Similarity	NPC194207
0.8148	Intermediate Similarity	NPC73243
0.8148	Intermediate Similarity	NPC309278
0.8148	Intermediate Similarity	NPC473328
0.8148	Intermediate Similarity	NPC300557
0.8148	Intermediate Similarity	NPC477809
0.8148	Intermediate Similarity	NPC150372
0.8148	Intermediate Similarity	NPC475333
0.8148	Intermediate Similarity	NPC46190
0.8148	Intermediate Similarity	NPC218571
0.8148	Intermediate Similarity	NPC6806
0.8148	Intermediate Similarity	NPC84956
0.8148	Intermediate Similarity	NPC102016
0.8148	Intermediate Similarity	NPC208383
0.8148	Intermediate Similarity	NPC95051
0.8148	Intermediate Similarity	NPC40440
0.8148	Intermediate Similarity	NPC473318
0.8148	Intermediate Similarity	NPC244086
0.8148	Intermediate Similarity	NPC249265
0.8148	Intermediate Similarity	NPC248746
0.8137	Intermediate Similarity	NPC90583
0.8131	Intermediate Similarity	NPC473469
0.8131	Intermediate Similarity	NPC33053
0.8131	Intermediate Similarity	NPC231340
0.8119	Intermediate Similarity	NPC477927
0.8119	Intermediate Similarity	NPC72817
0.8113	Intermediate Similarity	NPC31430
0.8113	Intermediate Similarity	NPC470885
0.8113	Intermediate Similarity	NPC187400
0.8113	Intermediate Similarity	NPC85593
0.8113	Intermediate Similarity	NPC474464
0.8113	Intermediate Similarity	NPC221562
0.8113	Intermediate Similarity	NPC312774
0.8113	Intermediate Similarity	NPC471111
0.8108	Intermediate Similarity	NPC32707
0.8108	Intermediate Similarity	NPC167183
0.8108	Intermediate Similarity	NPC11548
0.8108	Intermediate Similarity	NPC477810
0.81	Intermediate Similarity	NPC114389
0.8095	Intermediate Similarity	NPC136816
0.8091	Intermediate Similarity	NPC42171
0.8091	Intermediate Similarity	NPC477050
0.8091	Intermediate Similarity	NPC231797
0.8081	Intermediate Similarity	NPC477917
0.8081	Intermediate Similarity	NPC20822
0.8077	Intermediate Similarity	NPC324598
0.8077	Intermediate Similarity	NPC471247
0.8077	Intermediate Similarity	NPC7341
0.8077	Intermediate Similarity	NPC473200
0.8073	Intermediate Similarity	NPC23808
0.8073	Intermediate Similarity	NPC224314
0.8073	Intermediate Similarity	NPC269297
0.8073	Intermediate Similarity	NPC477811
0.8073	Intermediate Similarity	NPC222202
0.8073	Intermediate Similarity	NPC87998
0.8058	Intermediate Similarity	NPC473890
0.8058	Intermediate Similarity	NPC243728
0.8058	Intermediate Similarity	NPC76486
0.8056	Intermediate Similarity	NPC7213
0.8056	Intermediate Similarity	NPC128123
0.8056	Intermediate Similarity	NPC472896
0.8056	Intermediate Similarity	NPC472897
0.8053	Intermediate Similarity	NPC475403
0.8053	Intermediate Similarity	NPC476691
0.8053	Intermediate Similarity	NPC160888
0.8053	Intermediate Similarity	NPC476692
0.8037	Intermediate Similarity	NPC474569
0.8037	Intermediate Similarity	NPC470055
0.8037	Intermediate Similarity	NPC474015
0.8037	Intermediate Similarity	NPC470056
0.8036	Intermediate Similarity	NPC477029
0.8036	Intermediate Similarity	NPC477030
0.8019	Intermediate Similarity	NPC471886
0.8019	Intermediate Similarity	NPC471885
0.8019	Intermediate Similarity	NPC162354
0.8019	Intermediate Similarity	NPC471888
0.8019	Intermediate Similarity	NPC16573
0.8019	Intermediate Similarity	NPC471887
0.8018	Intermediate Similarity	NPC476546
0.8017	Intermediate Similarity	NPC257207
0.8017	Intermediate Similarity	NPC295133
0.8	Intermediate Similarity	NPC73385
0.8	Intermediate Similarity	NPC31346
0.8	Intermediate Similarity	NPC65034
0.8	Intermediate Similarity	NPC129372
0.8	Intermediate Similarity	NPC114188
0.8	Intermediate Similarity	NPC88000
0.8	Intermediate Similarity	NPC4831
0.8	Intermediate Similarity	NPC124677
0.8	Intermediate Similarity	NPC160734
0.8	Intermediate Similarity	NPC92710
0.8	Intermediate Similarity	NPC477028
0.8	Intermediate Similarity	NPC47566
0.8	Intermediate Similarity	NPC13193
0.8	Intermediate Similarity	NPC472023
0.8	Intermediate Similarity	NPC477032
0.8	Intermediate Similarity	NPC208189
0.8	Intermediate Similarity	NPC470168
0.8	Intermediate Similarity	NPC309425
0.7982	Intermediate Similarity	NPC476085
0.7982	Intermediate Similarity	NPC128133
0.7982	Intermediate Similarity	NPC472901
0.7982	Intermediate Similarity	NPC473633
0.7981	Intermediate Similarity	NPC158088
0.7981	Intermediate Similarity	NPC234287
0.7981	Intermediate Similarity	NPC280825
0.7965	Intermediate Similarity	NPC203862
0.7965	Intermediate Similarity	NPC20979
0.7963	Intermediate Similarity	NPC54619
0.7963	Intermediate Similarity	NPC190395
0.7963	Intermediate Similarity	NPC94272
0.7946	Intermediate Similarity	NPC208832
0.7944	Intermediate Similarity	NPC470057
0.7944	Intermediate Similarity	NPC470768
0.7944	Intermediate Similarity	NPC470062

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 NPC476595 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	2417
0.2-0.3	4168
0.3-0.4	1556
0.4-0.5	408
0.5-0.6	279
0.6-0.7	68
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7692	Intermediate Similarity	NPD8033	Approved
0.7672	Intermediate Similarity	NPD7516	Approved
0.7607	Intermediate Similarity	NPD8294	Approved
0.7607	Intermediate Similarity	NPD8377	Approved
0.7586	Intermediate Similarity	NPD7328	Approved
0.7586	Intermediate Similarity	NPD7327	Approved
0.7542	Intermediate Similarity	NPD8296	Approved
0.7542	Intermediate Similarity	NPD8335	Approved
0.7542	Intermediate Similarity	NPD8379	Approved
0.7542	Intermediate Similarity	NPD8380	Approved
0.7542	Intermediate Similarity	NPD8378	Approved
0.75	Intermediate Similarity	NPD8171	Discontinued
0.7345	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6412	Phase 2
0.725	Intermediate Similarity	NPD7503	Approved
0.7154	Intermediate Similarity	NPD7507	Approved
0.7049	Intermediate Similarity	NPD6370	Approved
0.7019	Intermediate Similarity	NPD7524	Approved
0.6984	Remote Similarity	NPD7319	Approved
0.696	Remote Similarity	NPD8293	Discontinued
0.6957	Remote Similarity	NPD6686	Approved
0.6917	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7736	Approved
0.6885	Remote Similarity	NPD6054	Approved
0.6885	Remote Similarity	NPD6059	Approved
0.6875	Remote Similarity	NPD4159	Approved
0.6855	Remote Similarity	NPD6067	Discontinued
0.6842	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6928	Phase 2
0.6822	Remote Similarity	NPD8449	Approved
0.6807	Remote Similarity	NPD8133	Approved
0.6786	Remote Similarity	NPD7640	Approved
0.6786	Remote Similarity	NPD7639	Approved
0.6769	Remote Similarity	NPD8450	Suspended
0.6731	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7638	Approved
0.6694	Remote Similarity	NPD6016	Approved
0.6694	Remote Similarity	NPD6015	Approved
0.6693	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.664	Remote Similarity	NPD5988	Approved
0.6635	Remote Similarity	NPD6695	Phase 3
0.6614	Remote Similarity	NPD6616	Approved
0.661	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4225	Approved
0.6542	Remote Similarity	NPD7750	Discontinued
0.6505	Remote Similarity	NPD7525	Registered
0.6457	Remote Similarity	NPD8328	Phase 3
0.6446	Remote Similarity	NPD6882	Approved
0.6446	Remote Similarity	NPD8297	Approved
0.6429	Remote Similarity	NPD8517	Approved
0.6429	Remote Similarity	NPD8515	Approved
0.6429	Remote Similarity	NPD8516	Approved
0.6429	Remote Similarity	NPD8513	Phase 3
0.6417	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6929	Approved
0.6385	Remote Similarity	NPD6033	Approved
0.6371	Remote Similarity	NPD6009	Approved
0.6349	Remote Similarity	NPD6319	Approved
0.6346	Remote Similarity	NPD6930	Phase 2
0.6346	Remote Similarity	NPD6931	Approved
0.6346	Remote Similarity	NPD4748	Discontinued
0.6337	Remote Similarity	NPD6942	Approved
0.6337	Remote Similarity	NPD7339	Approved
0.6312	Remote Similarity	NPD7625	Phase 1
0.6293	Remote Similarity	NPD5344	Discontinued
0.626	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD7320	Approved
0.625	Remote Similarity	NPD7645	Phase 2
0.624	Remote Similarity	NPD7115	Discovery
0.6218	Remote Similarity	NPD6008	Approved
0.6218	Remote Similarity	NPD6675	Approved
0.6218	Remote Similarity	NPD7128	Approved
0.6218	Remote Similarity	NPD5739	Approved
0.6218	Remote Similarity	NPD6402	Approved
0.6214	Remote Similarity	NPD5776	Phase 2
0.6214	Remote Similarity	NPD6925	Approved
0.6198	Remote Similarity	NPD6372	Approved
0.6198	Remote Similarity	NPD6373	Approved
0.619	Remote Similarity	NPD7514	Phase 3
0.6167	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7637	Suspended
0.6161	Remote Similarity	NPD7087	Discontinued
0.6154	Remote Similarity	NPD7145	Approved
0.614	Remote Similarity	NPD7991	Discontinued
0.6132	Remote Similarity	NPD6902	Approved
0.6117	Remote Similarity	NPD6933	Approved
0.6116	Remote Similarity	NPD6881	Approved
0.6116	Remote Similarity	NPD6899	Approved
0.6106	Remote Similarity	NPD6399	Phase 3
0.6102	Remote Similarity	NPD5211	Phase 2
0.61	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD8130	Phase 1
0.6098	Remote Similarity	NPD6650	Approved
0.6098	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6649	Approved
0.6091	Remote Similarity	NPD4250	Approved
0.6091	Remote Similarity	NPD4251	Approved
0.6071	Remote Similarity	NPD3168	Discontinued
0.6055	Remote Similarity	NPD6893	Approved
0.6038	Remote Similarity	NPD7332	Phase 2
0.6034	Remote Similarity	NPD4755	Approved
0.6033	Remote Similarity	NPD5701	Approved
0.6033	Remote Similarity	NPD5697	Approved
0.6019	Remote Similarity	NPD8264	Approved
0.6016	Remote Similarity	NPD4634	Approved
0.6016	Remote Similarity	NPD7102	Approved
0.6016	Remote Similarity	NPD7290	Approved
0.6016	Remote Similarity	NPD6883	Approved
0.6	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6051	Approved
0.5968	Remote Similarity	NPD6869	Approved
0.5968	Remote Similarity	NPD6617	Approved
0.5968	Remote Similarity	NPD6847	Approved
0.5965	Remote Similarity	NPD4202	Approved
0.5963	Remote Similarity	NPD4786	Approved
0.5963	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD7604	Phase 2
0.594	Remote Similarity	NPD8074	Phase 3
0.5935	Remote Similarity	NPD6013	Approved
0.5935	Remote Similarity	NPD6014	Approved
0.5935	Remote Similarity	NPD6012	Approved
0.5932	Remote Similarity	NPD5285	Approved
0.5932	Remote Similarity	NPD6648	Approved
0.5932	Remote Similarity	NPD4700	Approved
0.5932	Remote Similarity	NPD5286	Approved
0.5932	Remote Similarity	NPD4696	Approved
0.5926	Remote Similarity	NPD5956	Approved
0.5926	Remote Similarity	NPD3667	Approved
0.5923	Remote Similarity	NPD5983	Phase 2
0.5922	Remote Similarity	NPD6924	Approved
0.5922	Remote Similarity	NPD1810	Approved
0.5922	Remote Similarity	NPD4785	Approved
0.5922	Remote Similarity	NPD1811	Approved
0.5922	Remote Similarity	NPD6926	Approved
0.5922	Remote Similarity	NPD4784	Approved
0.592	Remote Similarity	NPD6053	Discontinued
0.5905	Remote Similarity	NPD6932	Approved
0.5902	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6083	Phase 2
0.5897	Remote Similarity	NPD6084	Phase 2
0.5882	Remote Similarity	NPD4243	Approved
0.5877	Remote Similarity	NPD8034	Phase 2
0.5877	Remote Similarity	NPD8035	Phase 2
0.5865	Remote Similarity	NPD6336	Discontinued
0.5856	Remote Similarity	NPD3618	Phase 1
0.5854	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD6011	Approved
0.5847	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5328	Approved
0.584	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5225	Approved
0.5833	Remote Similarity	NPD5226	Approved
0.5833	Remote Similarity	NPD5224	Approved
0.5833	Remote Similarity	NPD4633	Approved
0.5833	Remote Similarity	NPD6898	Phase 1
0.582	Remote Similarity	NPD6640	Phase 3
0.582	Remote Similarity	NPD4767	Approved
0.582	Remote Similarity	NPD4768	Approved
0.5818	Remote Similarity	NPD3133	Approved
0.5818	Remote Similarity	NPD3666	Approved
0.5818	Remote Similarity	NPD3665	Phase 1
0.5794	Remote Similarity	NPD6683	Phase 2
0.5789	Remote Similarity	NPD7838	Discovery
0.5785	Remote Similarity	NPD5175	Approved
0.5785	Remote Similarity	NPD5174	Approved
0.5776	Remote Similarity	NPD7748	Approved
0.5763	Remote Similarity	NPD7902	Approved
0.5752	Remote Similarity	NPD6903	Approved
0.575	Remote Similarity	NPD5223	Approved
0.5741	Remote Similarity	NPD7509	Discontinued
0.5741	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD6079	Approved
0.5739	Remote Similarity	NPD7983	Approved
0.5728	Remote Similarity	NPD7151	Approved
0.5728	Remote Similarity	NPD7152	Approved
0.5728	Remote Similarity	NPD7150	Approved
0.5726	Remote Similarity	NPD4730	Approved
0.5726	Remote Similarity	NPD4729	Approved
0.5726	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7146	Approved
0.5714	Remote Similarity	NPD6409	Approved
0.5714	Remote Similarity	NPD6684	Approved
0.5714	Remote Similarity	NPD7521	Approved
0.5714	Remote Similarity	NPD5330	Approved
0.5714	Remote Similarity	NPD7334	Approved
0.5702	Remote Similarity	NPD4753	Phase 2
0.5701	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD5357	Phase 1
0.569	Remote Similarity	NPD5778	Approved
0.569	Remote Similarity	NPD5779	Approved
0.5686	Remote Similarity	NPD6922	Approved
0.5686	Remote Similarity	NPD6923	Approved
0.5659	Remote Similarity	NPD6274	Approved
0.5656	Remote Similarity	NPD4754	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