NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	814.51
Volume:	821.372
LogP:	3.325
LogD:	3.427
LogS:	-3.477
# Rotatable Bonds:	16
TPSA:	217.22
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.105
Synthetic Accessibility Score:	6.338
Fsp3:	0.953
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:	-5.575
MDCK Permeability:	6.524153286591172e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.859
Human Intestinal Absorption (HIA):	0.331
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	94.99707794189453%
Volume Distribution (VD):	0.36
Pgp-substrate:	3.6065518856048584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.267
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.432
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.089
CYP3A4-substrate:	0.131

ADMET: Excretion

Clearance (CL):	0.79
Half-life (T1/2):	0.448

ADMET: Toxicity

hERG Blockers:	0.346
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.085
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC476594

Natural Product ID:	NPC476594
*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-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-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-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,5,6,7,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6,7-triol
Synonyms:	Anthenoside G
Standard InCHIKey:	FUWIMIQPBOPYNH-UTRGIAIQSA-N
Standard InCHI:	InChI=1S/C42H70O14/c1-19(2)20(3)9-10-21(4)30-28(16-24-29-23(12-14-42(24,30)6)41(5)13-11-22(43)15-25(41)31(46)32(29)47)53-40-35(50)38(37(55-40)27(45)18-52-8)56-39-34(49)33(48)36(54-39)26(44)17-51-7/h19,21-23,25-28,30-40,43-50H,3,9-18H2,1-2,4-8H3/t21-,22-,23+,25-,26+,27+,28-,30+,31+,32-,33-,34-,35-,36+,37+,38-,39+,40-,41-,42+/m1/s1
SMILES:	C[C@H](CCC(=C)C(C)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
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	46871840
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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	=	4600	nM	PMID[20184290]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	5500	nM	PMID[20184290]
NPT2	Others	Unspecified		IC50	>	25100	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 NPC476594 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	260
0.1-0.2	1884
0.2-0.3	5659
0.3-0.4	13355
0.4-0.5	9769
0.5-0.6	6388
0.6-0.7	4096
0.7-0.8	1198
0.8-0.85	81
0.85-0.9	3
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9796	High Similarity	NPC476595
0.9796	High Similarity	NPC476593
0.95	High Similarity	NPC476592
0.8835	High Similarity	NPC75608
0.8774	High Similarity	NPC141433
0.8667	High Similarity	NPC226642
0.8598	High Similarity	NPC247037
0.8585	High Similarity	NPC476538
0.8585	High Similarity	NPC476541
0.8585	High Similarity	NPC476539
0.8585	High Similarity	NPC476540
0.8571	High Similarity	NPC242748
0.8571	High Similarity	NPC26798
0.8571	High Similarity	NPC472899
0.8571	High Similarity	NPC472900
0.8571	High Similarity	NPC181845
0.8571	High Similarity	NPC472898
0.8558	High Similarity	NPC473198
0.8544	High Similarity	NPC470434
0.8532	High Similarity	NPC144068
0.8532	High Similarity	NPC476693
0.8532	High Similarity	NPC51154
0.8532	High Similarity	NPC307642
0.8529	High Similarity	NPC309493
0.8529	High Similarity	NPC5358
0.8529	High Similarity	NPC216260
0.8519	High Similarity	NPC13190
0.8519	High Similarity	NPC197231
0.8519	High Similarity	NPC476547
0.8505	High Similarity	NPC14630
0.8505	High Similarity	NPC70204
0.8505	High Similarity	NPC475670
0.8505	High Similarity	NPC306131
0.8505	High Similarity	NPC477026
0.8505	High Similarity	NPC157530
0.8505	High Similarity	NPC250089
0.8505	High Similarity	NPC477027
0.8491	Intermediate Similarity	NPC113044
0.8491	Intermediate Similarity	NPC470432
0.8491	Intermediate Similarity	NPC161676
0.8491	Intermediate Similarity	NPC14704
0.8491	Intermediate Similarity	NPC283829
0.8491	Intermediate Similarity	NPC230507
0.8491	Intermediate Similarity	NPC305423
0.8476	Intermediate Similarity	NPC475365
0.8476	Intermediate Similarity	NPC93352
0.8468	Intermediate Similarity	NPC100048
0.8468	Intermediate Similarity	NPC476690
0.8447	Intermediate Similarity	NPC91497
0.8447	Intermediate Similarity	NPC469942
0.8447	Intermediate Similarity	NPC64348
0.844	Intermediate Similarity	NPC263359
0.844	Intermediate Similarity	NPC244431
0.844	Intermediate Similarity	NPC216595
0.844	Intermediate Similarity	NPC112274
0.844	Intermediate Similarity	NPC19888
0.844	Intermediate Similarity	NPC32361
0.844	Intermediate Similarity	NPC473567
0.844	Intermediate Similarity	NPC254255
0.844	Intermediate Similarity	NPC31896
0.844	Intermediate Similarity	NPC210569
0.8431	Intermediate Similarity	NPC240372
0.8426	Intermediate Similarity	NPC103627
0.8426	Intermediate Similarity	NPC191439
0.8426	Intermediate Similarity	NPC170974
0.8426	Intermediate Similarity	NPC65155
0.8411	Intermediate Similarity	NPC98696
0.8396	Intermediate Similarity	NPC473476
0.8396	Intermediate Similarity	NPC473923
0.8393	Intermediate Similarity	NPC10366
0.8381	Intermediate Similarity	NPC475701
0.8381	Intermediate Similarity	NPC213190
0.8364	Intermediate Similarity	NPC79900
0.8349	Intermediate Similarity	NPC475247
0.8349	Intermediate Similarity	NPC294129
0.8333	Intermediate Similarity	NPC150372
0.8333	Intermediate Similarity	NPC476835
0.8333	Intermediate Similarity	NPC473328
0.8333	Intermediate Similarity	NPC244086
0.8333	Intermediate Similarity	NPC28844
0.8333	Intermediate Similarity	NPC90583
0.8333	Intermediate Similarity	NPC208383
0.8333	Intermediate Similarity	NPC477809
0.8333	Intermediate Similarity	NPC475333
0.8333	Intermediate Similarity	NPC300557
0.8333	Intermediate Similarity	NPC249265
0.8333	Intermediate Similarity	NPC84956
0.8333	Intermediate Similarity	NPC22779
0.8333	Intermediate Similarity	NPC171073
0.8333	Intermediate Similarity	NPC102016
0.8333	Intermediate Similarity	NPC46190
0.8333	Intermediate Similarity	NPC309278
0.8333	Intermediate Similarity	NPC224098
0.8333	Intermediate Similarity	NPC470433
0.8333	Intermediate Similarity	NPC6806
0.8333	Intermediate Similarity	NPC218571
0.8333	Intermediate Similarity	NPC95051
0.8333	Intermediate Similarity	NPC248746
0.8333	Intermediate Similarity	NPC73243
0.8333	Intermediate Similarity	NPC232054
0.8333	Intermediate Similarity	NPC40440
0.8333	Intermediate Similarity	NPC473318
0.8333	Intermediate Similarity	NPC42482
0.8333	Intermediate Similarity	NPC475550
0.8333	Intermediate Similarity	NPC194207
0.8318	Intermediate Similarity	NPC231340
0.8318	Intermediate Similarity	NPC473469
0.8318	Intermediate Similarity	NPC33053
0.8317	Intermediate Similarity	NPC72817
0.8317	Intermediate Similarity	NPC477927
0.8302	Intermediate Similarity	NPC470885
0.8302	Intermediate Similarity	NPC187400
0.8302	Intermediate Similarity	NPC85593
0.8302	Intermediate Similarity	NPC221562
0.8302	Intermediate Similarity	NPC312774
0.8302	Intermediate Similarity	NPC31430
0.8302	Intermediate Similarity	NPC474464
0.8288	Intermediate Similarity	NPC11548
0.8288	Intermediate Similarity	NPC167183
0.8288	Intermediate Similarity	NPC477810
0.8288	Intermediate Similarity	NPC32707
0.8286	Intermediate Similarity	NPC136816
0.8283	Intermediate Similarity	NPC477917
0.8273	Intermediate Similarity	NPC231797
0.8273	Intermediate Similarity	NPC42171
0.8273	Intermediate Similarity	NPC477050
0.8269	Intermediate Similarity	NPC324598
0.8269	Intermediate Similarity	NPC471247
0.8269	Intermediate Similarity	NPC473200
0.8269	Intermediate Similarity	NPC7341
0.8257	Intermediate Similarity	NPC222202
0.8257	Intermediate Similarity	NPC23808
0.8257	Intermediate Similarity	NPC477811
0.8257	Intermediate Similarity	NPC87998
0.8257	Intermediate Similarity	NPC224314
0.8257	Intermediate Similarity	NPC269297
0.8252	Intermediate Similarity	NPC473890
0.8252	Intermediate Similarity	NPC243728
0.8252	Intermediate Similarity	NPC76486
0.8241	Intermediate Similarity	NPC472897
0.8241	Intermediate Similarity	NPC472896
0.8241	Intermediate Similarity	NPC7213
0.823	Intermediate Similarity	NPC476691
0.823	Intermediate Similarity	NPC160888
0.823	Intermediate Similarity	NPC475403
0.823	Intermediate Similarity	NPC476692
0.8224	Intermediate Similarity	NPC474015
0.8224	Intermediate Similarity	NPC474569
0.8224	Intermediate Similarity	NPC470055
0.8224	Intermediate Similarity	NPC470056
0.8214	Intermediate Similarity	NPC477029
0.8214	Intermediate Similarity	NPC477030
0.8208	Intermediate Similarity	NPC471888
0.8208	Intermediate Similarity	NPC471886
0.8208	Intermediate Similarity	NPC162354
0.8208	Intermediate Similarity	NPC471885
0.8208	Intermediate Similarity	NPC16573
0.8208	Intermediate Similarity	NPC471887
0.8198	Intermediate Similarity	NPC476546
0.819	Intermediate Similarity	NPC472023
0.819	Intermediate Similarity	NPC309425
0.819	Intermediate Similarity	NPC160734
0.819	Intermediate Similarity	NPC88000
0.819	Intermediate Similarity	NPC470168
0.819	Intermediate Similarity	NPC31346
0.819	Intermediate Similarity	NPC4831
0.819	Intermediate Similarity	NPC295133
0.819	Intermediate Similarity	NPC47566
0.819	Intermediate Similarity	NPC129372
0.819	Intermediate Similarity	NPC257207
0.8182	Intermediate Similarity	NPC124677
0.8182	Intermediate Similarity	NPC477032
0.8182	Intermediate Similarity	NPC114188
0.8182	Intermediate Similarity	NPC65034
0.8182	Intermediate Similarity	NPC13193
0.8182	Intermediate Similarity	NPC477028
0.8182	Intermediate Similarity	NPC208189
0.8173	Intermediate Similarity	NPC234287
0.8173	Intermediate Similarity	NPC280825
0.8173	Intermediate Similarity	NPC275865
0.8173	Intermediate Similarity	NPC158088
0.8165	Intermediate Similarity	NPC128133
0.8165	Intermediate Similarity	NPC472901
0.8158	Intermediate Similarity	NPC476085
0.8158	Intermediate Similarity	NPC473633
0.8148	Intermediate Similarity	NPC94272
0.8148	Intermediate Similarity	NPC190395
0.8148	Intermediate Similarity	NPC54619
0.8142	Intermediate Similarity	NPC20979
0.8142	Intermediate Similarity	NPC203862
0.8131	Intermediate Similarity	NPC273879
0.8131	Intermediate Similarity	NPC165033
0.8131	Intermediate Similarity	NPC470768
0.8131	Intermediate Similarity	NPC475521
0.8131	Intermediate Similarity	NPC471111
0.8125	Intermediate Similarity	NPC208832
0.8113	Intermediate Similarity	NPC37207
0.8113	Intermediate Similarity	NPC471482
0.8113	Intermediate Similarity	NPC159036
0.8113	Intermediate Similarity	NPC288694

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 NPC476594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	2136
0.2-0.3	4222
0.3-0.4	1735
0.4-0.5	467
0.5-0.6	266
0.6-0.7	98
0.7-0.8	20
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
0.7863	Intermediate Similarity	NPD8033	Approved
0.7845	Intermediate Similarity	NPD7516	Approved
0.7778	Intermediate Similarity	NPD8294	Approved
0.7778	Intermediate Similarity	NPD8377	Approved
0.7759	Intermediate Similarity	NPD7328	Approved
0.7759	Intermediate Similarity	NPD7327	Approved
0.7712	Intermediate Similarity	NPD8380	Approved
0.7712	Intermediate Similarity	NPD8379	Approved
0.7712	Intermediate Similarity	NPD8378	Approved
0.7712	Intermediate Similarity	NPD8335	Approved
0.7712	Intermediate Similarity	NPD8296	Approved
0.75	Intermediate Similarity	NPD6412	Phase 2
0.7417	Intermediate Similarity	NPD7503	Approved
0.7358	Intermediate Similarity	NPD8171	Discontinued
0.7317	Intermediate Similarity	NPD7507	Approved
0.7217	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6370	Approved
0.7212	Intermediate Similarity	NPD7524	Approved
0.7143	Intermediate Similarity	NPD7319	Approved
0.713	Intermediate Similarity	NPD6686	Approved
0.712	Intermediate Similarity	NPD8293	Discontinued
0.7063	Intermediate Similarity	NPD7736	Approved
0.7049	Intermediate Similarity	NPD6059	Approved
0.7049	Intermediate Similarity	NPD6054	Approved
0.7016	Intermediate Similarity	NPD6067	Discontinued
0.6977	Remote Similarity	NPD8449	Approved
0.6975	Remote Similarity	NPD8133	Approved
0.6964	Remote Similarity	NPD7639	Approved
0.6964	Remote Similarity	NPD7640	Approved
0.6923	Remote Similarity	NPD8450	Suspended
0.6923	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7638	Approved
0.6855	Remote Similarity	NPD6015	Approved
0.6855	Remote Similarity	NPD6016	Approved
0.685	Remote Similarity	NPD7078	Approved
0.6827	Remote Similarity	NPD6695	Phase 3
0.6825	Remote Similarity	NPD7492	Approved
0.6803	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5988	Approved
0.6772	Remote Similarity	NPD6616	Approved
0.6754	Remote Similarity	NPD4159	Approved
0.6729	Remote Similarity	NPD7750	Discontinued
0.6726	Remote Similarity	NPD4225	Approved
0.6724	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6928	Phase 2
0.6699	Remote Similarity	NPD7525	Registered
0.6614	Remote Similarity	NPD8328	Phase 3
0.6612	Remote Similarity	NPD6882	Approved
0.6612	Remote Similarity	NPD8297	Approved
0.6602	Remote Similarity	NPD6929	Approved
0.6587	Remote Similarity	NPD8516	Approved
0.6587	Remote Similarity	NPD8515	Approved
0.6587	Remote Similarity	NPD8513	Phase 3
0.6587	Remote Similarity	NPD8517	Approved
0.6552	Remote Similarity	NPD7632	Discontinued
0.6538	Remote Similarity	NPD6931	Approved
0.6538	Remote Similarity	NPD6033	Approved
0.6538	Remote Similarity	NPD6930	Phase 2
0.6535	Remote Similarity	NPD7339	Approved
0.6535	Remote Similarity	NPD6942	Approved
0.6532	Remote Similarity	NPD6009	Approved
0.6508	Remote Similarity	NPD6319	Approved
0.65	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5344	Discontinued
0.6454	Remote Similarity	NPD7625	Phase 1
0.6442	Remote Similarity	NPD7645	Phase 2
0.6423	Remote Similarity	NPD4632	Approved
0.6417	Remote Similarity	NPD7320	Approved
0.6408	Remote Similarity	NPD5776	Phase 2
0.6408	Remote Similarity	NPD6925	Approved
0.64	Remote Similarity	NPD7115	Discovery
0.6387	Remote Similarity	NPD6402	Approved
0.6387	Remote Similarity	NPD5739	Approved
0.6387	Remote Similarity	NPD6675	Approved
0.6387	Remote Similarity	NPD6008	Approved
0.6387	Remote Similarity	NPD7128	Approved
0.6381	Remote Similarity	NPD7514	Phase 3
0.6364	Remote Similarity	NPD6373	Approved
0.6364	Remote Similarity	NPD6372	Approved
0.6346	Remote Similarity	NPD7145	Approved
0.6339	Remote Similarity	NPD7087	Discontinued
0.6339	Remote Similarity	NPD7637	Suspended
0.6321	Remote Similarity	NPD6902	Approved
0.6311	Remote Similarity	NPD6933	Approved
0.6311	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6399	Phase 3
0.6281	Remote Similarity	NPD6881	Approved
0.6281	Remote Similarity	NPD6899	Approved
0.6273	Remote Similarity	NPD4250	Approved
0.6273	Remote Similarity	NPD4251	Approved
0.6271	Remote Similarity	NPD5211	Phase 2
0.626	Remote Similarity	NPD6649	Approved
0.626	Remote Similarity	NPD8130	Phase 1
0.626	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6650	Approved
0.625	Remote Similarity	NPD3168	Discontinued
0.6239	Remote Similarity	NPD6893	Approved
0.6226	Remote Similarity	NPD7332	Phase 2
0.6226	Remote Similarity	NPD4748	Discontinued
0.6214	Remote Similarity	NPD8264	Approved
0.6207	Remote Similarity	NPD4755	Approved
0.6198	Remote Similarity	NPD5697	Approved
0.6198	Remote Similarity	NPD5701	Approved
0.6182	Remote Similarity	NPD4249	Approved
0.6179	Remote Similarity	NPD4634	Approved
0.6179	Remote Similarity	NPD7290	Approved
0.6179	Remote Similarity	NPD6883	Approved
0.6179	Remote Similarity	NPD7102	Approved
0.6167	Remote Similarity	NPD5141	Approved
0.6161	Remote Similarity	NPD6051	Approved
0.6147	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD4786	Approved
0.614	Remote Similarity	NPD4202	Approved
0.6129	Remote Similarity	NPD6847	Approved
0.6129	Remote Similarity	NPD6617	Approved
0.6129	Remote Similarity	NPD6869	Approved
0.6117	Remote Similarity	NPD6926	Approved
0.6117	Remote Similarity	NPD4785	Approved
0.6117	Remote Similarity	NPD6924	Approved
0.6117	Remote Similarity	NPD4784	Approved
0.6111	Remote Similarity	NPD3667	Approved
0.6107	Remote Similarity	NPD7604	Phase 2
0.6102	Remote Similarity	NPD5285	Approved
0.6102	Remote Similarity	NPD6648	Approved
0.6102	Remote Similarity	NPD5286	Approved
0.6102	Remote Similarity	NPD4700	Approved
0.6102	Remote Similarity	NPD4696	Approved
0.6098	Remote Similarity	NPD6012	Approved
0.6098	Remote Similarity	NPD6013	Approved
0.6098	Remote Similarity	NPD6014	Approved
0.6095	Remote Similarity	NPD6932	Approved
0.609	Remote Similarity	NPD8074	Phase 3
0.608	Remote Similarity	NPD6053	Discontinued
0.6078	Remote Similarity	NPD4243	Approved
0.6077	Remote Similarity	NPD5983	Phase 2
0.6074	Remote Similarity	NPD5956	Approved
0.6068	Remote Similarity	NPD6084	Phase 2
0.6068	Remote Similarity	NPD6083	Phase 2
0.6066	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD8035	Phase 2
0.6053	Remote Similarity	NPD8034	Phase 2
0.6036	Remote Similarity	NPD3618	Phase 1
0.6034	Remote Similarity	NPD7991	Discontinued
0.6019	Remote Similarity	NPD6898	Phase 1
0.6018	Remote Similarity	NPD5328	Approved
0.6017	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6011	Approved
0.6015	Remote Similarity	NPD6336	Discontinued
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD5224	Approved
0.5984	Remote Similarity	NPD4767	Approved
0.5984	Remote Similarity	NPD6640	Phase 3
0.5984	Remote Similarity	NPD4768	Approved
0.5981	Remote Similarity	NPD6683	Phase 2
0.598	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD7838	Discovery
0.595	Remote Similarity	NPD5175	Approved
0.595	Remote Similarity	NPD5174	Approved
0.5948	Remote Similarity	NPD7748	Approved
0.5932	Remote Similarity	NPD7902	Approved
0.5929	Remote Similarity	NPD6903	Approved
0.5926	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7509	Discontinued
0.5922	Remote Similarity	NPD7151	Approved
0.5922	Remote Similarity	NPD7152	Approved
0.5922	Remote Similarity	NPD7150	Approved
0.5917	Remote Similarity	NPD5223	Approved
0.5913	Remote Similarity	NPD6079	Approved
0.5913	Remote Similarity	NPD7983	Approved
0.5897	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6684	Approved
0.5893	Remote Similarity	NPD5330	Approved
0.5893	Remote Similarity	NPD7521	Approved
0.5893	Remote Similarity	NPD7334	Approved
0.5893	Remote Similarity	NPD6409	Approved
0.5893	Remote Similarity	NPD7146	Approved
0.5888	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD4730	Approved
0.5887	Remote Similarity	NPD4729	Approved
0.5887	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6923	Approved
0.5882	Remote Similarity	NPD6922	Approved
0.5882	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD4753	Phase 2
0.5862	Remote Similarity	NPD5779	Approved
0.5862	Remote Similarity	NPD5778	Approved
0.5854	Remote Similarity	NPD5357	Phase 1
0.5826	Remote Similarity	NPD46	Approved
0.5826	Remote Similarity	NPD6698	Approved
0.5825	Remote Similarity	NPD7144	Approved
0.5825	Remote Similarity	NPD7143	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