NPASS Compound

Structure

NPC473012 OpenBabel07101719512D 48 53 0 0 1 0 0 0 0 0999 V2000 -2.4665 -0.6782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3165 -2.1504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0835 -3.1319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7834 -3.1319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6165 -2.1504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0835 -1.1689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0491 -0.0560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0491 1.6440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0306 -0.0560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0306 1.6440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0334 -1.6597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1834 -1.1689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3534 3.2509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2633 2.7256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7834 -1.1689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9099 4.3884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8834 -0.1874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3334 1.2848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4665 -1.6597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9334 -2.6411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5584 0.7940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9334 -1.6597 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.3033 2.5215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5213 0.7940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8834 -1.1689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0502 4.1843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5666 3.6590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1834 -0.1874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7834 -0.1874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0334 0.3033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4834 1.7755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3334 0.3033 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.5881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6334 1.2848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9334 1.2848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7834 1.7755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5769 0.7940 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6334 0.3033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9334 0.3033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5028 0.7940 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7333 -1.6597 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7069 4.9137 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5267 3.8631 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0334 1.2848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4834 2.7570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7834 2.7570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4834 -0.1874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 5 19 2 0 0 0 0 6 22 1 0 0 0 0 7 9 1 0 0 0 0 7 21 2 0 0 0 0 8 10 2 0 0 0 0 8 21 1 0 0 0 0 9 24 2 0 0 0 0 10 24 1 0 0 0 0 11 12 2 0 0 0 0 11 25 1 0 0 0 0 12 28 1 0 0 0 0 13 23 2 0 0 0 0 13 26 1 0 0 0 0 14 23 1 0 0 0 0 14 27 2 0 0 0 0 15 22 1 0 0 0 0 15 29 1 0 0 0 0 16 26 2 0 0 0 0 16 27 1 0 0 0 0 17 25 2 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 18 32 1 0 0 0 0 20 22 1 0 0 0 0 24 40 1 0 0 0 0 25 41 1 0 0 0 0 26 42 1 0 0 0 0 27 43 1 0 0 0 0 28 30 2 0 0 0 0 29 38 1 0 0 0 0 29 39 2 0 0 0 0 30 44 1 0 0 0 0 31 34 1 0 0 0 0 31 45 2 0 0 0 0 32 28 1 1 0 0 0 32 47 1 0 0 0 0 33 23 1 1 0 0 0 33 35 1 0 0 0 0 33 37 1 0 0 0 0 34 36 1 0 0 0 0 34 38 2 0 0 0 0 35 36 2 0 0 0 0 35 39 1 0 0 0 0 36 46 1 0 0 0 0 37 21 1 1 0 0 0 37 48 1 0 0 0 0 38 47 1 0 0 0 0 39 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	650.25
Volume:	671.326
LogP:	7.805
LogD:	4.084
LogS:	-3.115
# Rotatable Bonds:	8
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.104
Synthetic Accessibility Score:	4.747
Fsp3:	0.256
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.1
MDCK Permeability:	8.85819554241607e-06
Pgp-inhibitor:	0.186
Pgp-substrate:	0.221
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	96.04010772705078%
Volume Distribution (VD):	0.559
Pgp-substrate:	1.442967176437378%

ADMET: Metabolism

CYP1A2-inhibitor:	0.101
CYP1A2-substrate:	0.446
CYP2C19-inhibitor:	0.961
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.936
CYP2C9-substrate:	0.993
CYP2D6-inhibitor:	0.788
CYP2D6-substrate:	0.717
CYP3A4-inhibitor:	0.42
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	13.187
Half-life (T1/2):	0.236

ADMET: Toxicity

hERG Blockers:	0.135
Human Hepatotoxicity (H-HT):	0.932
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.868
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.95
Carcinogencity:	0.086
Eye Corrosion:	0.003
Eye Irritation:	0.887
Respiratory Toxicity:	0.583

Download Data

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

Natural Product: NPC473012

Natural Product ID:	NPC473012
*Common Name:**	Alopecurone B
IUPAC Name:	(2R,3S,7S)-7-(2,4-dihydroxyphenyl)-3-(3,5-dihydroxyphenyl)-4-hydroxy-2-(4-hydroxyphenyl)-9-(5-methyl-2-prop-1-en-2-ylhex-4-enyl)-2,3,6,7-tetrahydrofuro[3,2-g]chromen-5-one
Synonyms:
Standard InCHIKey:	UVQKYQGWGMUDAI-PFVCLYDRSA-N
Standard InCHI:	InChI=1S/C39H38O9/c1-19(2)5-6-22(20(3)4)15-29-38-34(31(45)18-32(47-38)28-12-11-25(41)17-30(28)44)36(46)35-33(23-13-26(42)16-27(43)14-23)37(48-39(29)35)21-7-9-24(40)10-8-21/h5,7-14,16-17,22,32-33,37,40-44,46H,3,6,15,18H2,1-2,4H3/t22?,32-,33-,37-/m0/s1
SMILES:	CC(=CCC(C(=C)C)Cc1c2O[C@@H](CC(=O)c2c(c2c1O[C@H]([C@H]2c1cc(O)cc(c1)O)c1ccc(cc1)O)O)c1ccc(cc1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3600405
PubChem CID:	10394489
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	root bark	Mongolian	n.a.	PMID[26073007]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[31747283]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20471	Sophora alopecuroides	Species	Fabaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	15900.0	nM	PMID[480340]

☑ 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 NPC473012 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	406
0.1-0.2	1529
0.2-0.3	3244
0.3-0.4	8708
0.4-0.5	10190
0.5-0.6	3553
0.6-0.7	5417
0.7-0.8	5627
0.8-0.85	2606
0.85-0.9	1157
0.9-0.95	231
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC312273
0.9935	High Similarity	NPC301256
0.9935	High Similarity	NPC473009
0.9871	High Similarity	NPC473010
0.9615	High Similarity	NPC473011
0.961	High Similarity	NPC1796
0.961	High Similarity	NPC257166
0.9557	High Similarity	NPC251336
0.9548	High Similarity	NPC15815
0.9548	High Similarity	NPC51247
0.9542	High Similarity	NPC121568
0.9487	High Similarity	NPC42965
0.9487	High Similarity	NPC98023
0.9487	High Similarity	NPC195136
0.9487	High Similarity	NPC226462
0.9484	High Similarity	NPC475184
0.9481	High Similarity	NPC79375
0.9481	High Similarity	NPC37253
0.9423	High Similarity	NPC105584
0.9419	High Similarity	NPC32867
0.9419	High Similarity	NPC69531
0.9412	High Similarity	NPC178484
0.9363	High Similarity	NPC121647
0.9359	High Similarity	NPC208258
0.9359	High Similarity	NPC323627
0.9359	High Similarity	NPC318527
0.9359	High Similarity	NPC324358
0.9359	High Similarity	NPC287789
0.9359	High Similarity	NPC322459
0.9359	High Similarity	NPC271741
0.9355	High Similarity	NPC134171
0.9355	High Similarity	NPC182555
0.9355	High Similarity	NPC300668
0.9355	High Similarity	NPC66441
0.9351	High Similarity	NPC115601
0.9351	High Similarity	NPC78324
0.9351	High Similarity	NPC208011
0.9351	High Similarity	NPC39154
0.9321	High Similarity	NPC477529
0.9304	High Similarity	NPC18380
0.9299	High Similarity	NPC51760
0.9299	High Similarity	NPC295090
0.9295	High Similarity	NPC61112
0.9295	High Similarity	NPC198489
0.9281	High Similarity	NPC3642
0.9255	High Similarity	NPC286230
0.9255	High Similarity	NPC253730
0.9245	High Similarity	NPC15374
0.9241	High Similarity	NPC292863
0.9241	High Similarity	NPC184326
0.9231	High Similarity	NPC265624
0.9231	High Similarity	NPC14606
0.9231	High Similarity	NPC201227
0.9231	High Similarity	NPC159707
0.9231	High Similarity	NPC258474
0.9231	High Similarity	NPC186227
0.9231	High Similarity	NPC205026
0.9231	High Similarity	NPC150908
0.9231	High Similarity	NPC158027
0.9231	High Similarity	NPC215203
0.9231	High Similarity	NPC52611
0.9231	High Similarity	NPC100049
0.9231	High Similarity	NPC121649
0.9231	High Similarity	NPC248739
0.9226	High Similarity	NPC43345
0.9226	High Similarity	NPC174086
0.9216	High Similarity	NPC122894
0.9193	High Similarity	NPC171985
0.9193	High Similarity	NPC320741
0.9193	High Similarity	NPC224851
0.9187	High Similarity	NPC38591
0.9182	High Similarity	NPC137232
0.9177	High Similarity	NPC18699
0.9177	High Similarity	NPC55443
0.9177	High Similarity	NPC195167
0.9172	High Similarity	NPC309648
0.9172	High Similarity	NPC56049
0.9172	High Similarity	NPC54830
0.9167	High Similarity	NPC71061
0.9167	High Similarity	NPC290830
0.9167	High Similarity	NPC303485
0.9167	High Similarity	NPC72425
0.9167	High Similarity	NPC324447
0.9167	High Similarity	NPC194593
0.9161	High Similarity	NPC476552
0.9161	High Similarity	NPC476551
0.9161	High Similarity	NPC476553
0.9156	High Similarity	NPC132345
0.915	High Similarity	NPC475348
0.915	High Similarity	NPC261271
0.913	High Similarity	NPC469664
0.913	High Similarity	NPC169471
0.9097	High Similarity	NPC472633
0.9091	High Similarity	NPC152233
0.9091	High Similarity	NPC145467
0.9091	High Similarity	NPC300657
0.9085	High Similarity	NPC290133
0.9085	High Similarity	NPC24136
0.9085	High Similarity	NPC470133
0.9085	High Similarity	NPC473078
0.9085	High Similarity	NPC109183
0.9085	High Similarity	NPC228779
0.9085	High Similarity	NPC470134
0.9085	High Similarity	NPC187282
0.9085	High Similarity	NPC470131
0.9085	High Similarity	NPC470132
0.908	High Similarity	NPC475212
0.908	High Similarity	NPC107627
0.9074	High Similarity	NPC82330
0.9068	High Similarity	NPC290160
0.9068	High Similarity	NPC63438
0.9062	High Similarity	NPC273467
0.9062	High Similarity	NPC189552
0.9057	High Similarity	NPC123544
0.9051	High Similarity	NPC208152
0.9051	High Similarity	NPC78492
0.9048	High Similarity	NPC150977
0.9038	High Similarity	NPC204561
0.9038	High Similarity	NPC309512
0.9038	High Similarity	NPC67322
0.9038	High Similarity	NPC317715
0.9038	High Similarity	NPC222713
0.9038	High Similarity	NPC148945
0.9038	High Similarity	NPC138299
0.9038	High Similarity	NPC78835
0.9038	High Similarity	NPC111112
0.9038	High Similarity	NPC316960
0.9036	High Similarity	NPC101991
0.9032	High Similarity	NPC473016
0.9026	High Similarity	NPC308200
0.9024	High Similarity	NPC279209
0.9024	High Similarity	NPC102277
0.902	High Similarity	NPC470136
0.902	High Similarity	NPC194949
0.902	High Similarity	NPC470135
0.902	High Similarity	NPC235217
0.902	High Similarity	NPC473014
0.902	High Similarity	NPC271288
0.902	High Similarity	NPC282957
0.902	High Similarity	NPC39045
0.9012	High Similarity	NPC477840
0.9006	High Similarity	NPC261896
0.9006	High Similarity	NPC310603
0.9	High Similarity	NPC47905
0.9	High Similarity	NPC312993
0.9	High Similarity	NPC73929
0.9	High Similarity	NPC139683
0.9	High Similarity	NPC186325
0.8987	High Similarity	NPC254351
0.8974	High Similarity	NPC29777
0.8974	High Similarity	NPC471115
0.8974	High Similarity	NPC321896
0.8974	High Similarity	NPC476185
0.897	High Similarity	NPC257667
0.897	High Similarity	NPC472454
0.897	High Similarity	NPC186847
0.8968	High Similarity	NPC106328
0.8968	High Similarity	NPC168085
0.8968	High Similarity	NPC35150
0.8968	High Similarity	NPC39195
0.8963	High Similarity	NPC53252
0.8963	High Similarity	NPC300307
0.8961	High Similarity	NPC127059
0.8961	High Similarity	NPC285630
0.8961	High Similarity	NPC472629
0.8954	High Similarity	NPC107177
0.8954	High Similarity	NPC77794
0.8954	High Similarity	NPC278249
0.8954	High Similarity	NPC223812
0.8954	High Similarity	NPC185276
0.8954	High Similarity	NPC85162
0.8954	High Similarity	NPC125894
0.8954	High Similarity	NPC81697
0.8951	High Similarity	NPC159508
0.8944	High Similarity	NPC92589
0.8944	High Similarity	NPC142252
0.8941	High Similarity	NPC304322
0.8938	High Similarity	NPC90497
0.8938	High Similarity	NPC472617
0.8938	High Similarity	NPC177650
0.8938	High Similarity	NPC40583
0.8931	High Similarity	NPC192587
0.8929	High Similarity	NPC121888
0.8924	High Similarity	NPC213608
0.8924	High Similarity	NPC1477
0.8917	High Similarity	NPC472636
0.8916	High Similarity	NPC24748
0.8916	High Similarity	NPC17105
0.8916	High Similarity	NPC474276
0.8916	High Similarity	NPC147363
0.8916	High Similarity	NPC73899
0.8916	High Similarity	NPC59491
0.8916	High Similarity	NPC168789
0.891	High Similarity	NPC471114
0.891	High Similarity	NPC317492
0.891	High Similarity	NPC291746
0.891	High Similarity	NPC288840
0.8909	High Similarity	NPC287884
0.8909	High Similarity	NPC180768
0.8909	High Similarity	NPC8704

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 NPC473012 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	936
0.2-0.3	1522
0.3-0.4	2587
0.4-0.5	1975
0.5-0.6	1097
0.6-0.7	464
0.7-0.8	166
0.8-0.85	31
0.85-0.9	18
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9355	High Similarity	NPD8443	Clinical (unspecified phase)
0.9182	High Similarity	NPD6959	Discontinued
0.8896	High Similarity	NPD7852	Clinical (unspecified phase)
0.8805	High Similarity	NPD2393	Clinical (unspecified phase)
0.8805	High Similarity	NPD7819	Suspended
0.8696	High Similarity	NPD7768	Phase 2
0.8679	High Similarity	NPD7411	Suspended
0.8667	High Similarity	NPD6166	Phase 2
0.8667	High Similarity	NPD6167	Clinical (unspecified phase)
0.8667	High Similarity	NPD6168	Clinical (unspecified phase)
0.8654	High Similarity	NPD4378	Clinical (unspecified phase)
0.8654	High Similarity	NPD7410	Clinical (unspecified phase)
0.8616	High Similarity	NPD4380	Phase 2
0.8562	High Similarity	NPD1550	Clinical (unspecified phase)
0.8562	High Similarity	NPD1552	Clinical (unspecified phase)
0.8537	High Similarity	NPD5494	Approved
0.8528	High Similarity	NPD7075	Discontinued
0.8512	High Similarity	NPD7804	Clinical (unspecified phase)
0.8509	High Similarity	NPD1934	Approved
0.8506	High Similarity	NPD1549	Phase 2
0.8353	Intermediate Similarity	NPD7074	Phase 3
0.8344	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD3749	Approved
0.8303	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD7054	Approved
0.8284	Intermediate Similarity	NPD7473	Discontinued
0.8258	Intermediate Similarity	NPD2796	Approved
0.8256	Intermediate Similarity	NPD6559	Discontinued
0.8246	Intermediate Similarity	NPD7472	Approved
0.8242	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7390	Discontinued
0.8208	Intermediate Similarity	NPD7808	Phase 3
0.8198	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1510	Phase 2
0.8161	Intermediate Similarity	NPD8312	Approved
0.8161	Intermediate Similarity	NPD8313	Approved
0.815	Intermediate Similarity	NPD7251	Discontinued
0.8133	Intermediate Similarity	NPD3882	Suspended
0.8129	Intermediate Similarity	NPD3818	Discontinued
0.8125	Intermediate Similarity	NPD1511	Approved
0.8121	Intermediate Similarity	NPD2801	Approved
0.8107	Intermediate Similarity	NPD6232	Discontinued
0.8101	Intermediate Similarity	NPD2800	Approved
0.8092	Intermediate Similarity	NPD6797	Phase 2
0.8081	Intermediate Similarity	NPD5844	Phase 1
0.8075	Intermediate Similarity	NPD2534	Approved
0.8075	Intermediate Similarity	NPD2533	Approved
0.8075	Intermediate Similarity	NPD2532	Approved
0.8061	Intermediate Similarity	NPD6801	Discontinued
0.8052	Intermediate Similarity	NPD1240	Approved
0.8039	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1512	Approved
0.7987	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD3817	Phase 2
0.7949	Intermediate Similarity	NPD1607	Approved
0.7944	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD4908	Phase 1
0.7898	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD6651	Approved
0.7833	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3750	Approved
0.7799	Intermediate Similarity	NPD2935	Discontinued
0.7799	Intermediate Similarity	NPD6100	Approved
0.7799	Intermediate Similarity	NPD6099	Approved
0.7798	Intermediate Similarity	NPD8455	Phase 2
0.7797	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6799	Approved
0.7791	Intermediate Similarity	NPD7229	Phase 3
0.7771	Intermediate Similarity	NPD3226	Approved
0.7758	Intermediate Similarity	NPD920	Approved
0.7751	Intermediate Similarity	NPD5402	Approved
0.775	Intermediate Similarity	NPD2344	Approved
0.7725	Intermediate Similarity	NPD6599	Discontinued
0.7692	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD4363	Phase 3
0.7663	Intermediate Similarity	NPD4360	Phase 2
0.7654	Intermediate Similarity	NPD1243	Approved
0.7651	Intermediate Similarity	NPD5403	Approved
0.7644	Intermediate Similarity	NPD3926	Phase 2
0.7636	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2799	Discontinued
0.7625	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD8151	Discontinued
0.7586	Intermediate Similarity	NPD5711	Approved
0.7586	Intermediate Similarity	NPD5710	Approved
0.7584	Intermediate Similarity	NPD5953	Discontinued
0.7581	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD7871	Phase 2
0.7579	Intermediate Similarity	NPD7870	Phase 2
0.7578	Intermediate Similarity	NPD1551	Phase 2
0.7571	Intermediate Similarity	NPD7286	Phase 2
0.7569	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2309	Approved
0.756	Intermediate Similarity	NPD7458	Discontinued
0.7545	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2346	Discontinued
0.753	Intermediate Similarity	NPD5401	Approved
0.7529	Intermediate Similarity	NPD1247	Approved
0.7529	Intermediate Similarity	NPD7199	Phase 2
0.7527	Intermediate Similarity	NPD8150	Discontinued
0.7526	Intermediate Similarity	NPD7697	Approved
0.7526	Intermediate Similarity	NPD7696	Phase 3
0.7526	Intermediate Similarity	NPD7698	Approved
0.7516	Intermediate Similarity	NPD3748	Approved
0.7514	Intermediate Similarity	NPD7228	Approved
0.7514	Intermediate Similarity	NPD919	Approved
0.7486	Intermediate Similarity	NPD3787	Discontinued
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7471	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD5405	Approved
0.7469	Intermediate Similarity	NPD5406	Approved
0.7469	Intermediate Similarity	NPD5404	Approved
0.7469	Intermediate Similarity	NPD5408	Approved
0.746	Intermediate Similarity	NPD6780	Approved
0.746	Intermediate Similarity	NPD6779	Approved
0.746	Intermediate Similarity	NPD6777	Approved
0.746	Intermediate Similarity	NPD6776	Approved
0.746	Intermediate Similarity	NPD6782	Approved
0.746	Intermediate Similarity	NPD6781	Approved
0.746	Intermediate Similarity	NPD6778	Approved
0.7451	Intermediate Similarity	NPD1610	Phase 2
0.7443	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7783	Phase 2
0.7435	Intermediate Similarity	NPD7435	Discontinued
0.7433	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD4361	Phase 2
0.7432	Intermediate Similarity	NPD8434	Phase 2
0.7427	Intermediate Similarity	NPD37	Approved
0.7425	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD3751	Discontinued
0.7414	Intermediate Similarity	NPD6234	Discontinued
0.7399	Intermediate Similarity	NPD4966	Approved
0.7399	Intermediate Similarity	NPD4965	Approved
0.7399	Intermediate Similarity	NPD4967	Phase 2
0.7394	Intermediate Similarity	NPD7003	Approved
0.7394	Intermediate Similarity	NPD4628	Phase 3
0.7389	Intermediate Similarity	NPD2861	Phase 2
0.7384	Intermediate Similarity	NPD5761	Phase 2
0.7384	Intermediate Similarity	NPD5760	Phase 2
0.7381	Intermediate Similarity	NPD6273	Approved
0.7371	Intermediate Similarity	NPD7701	Phase 2
0.7368	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2313	Discontinued
0.7351	Intermediate Similarity	NPD4287	Approved
0.7347	Intermediate Similarity	NPD7801	Approved
0.7342	Intermediate Similarity	NPD6832	Phase 2
0.7338	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5124	Phase 1
0.7318	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7177	Discontinued
0.7317	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7033	Discontinued
0.7296	Intermediate Similarity	NPD4625	Phase 3
0.7296	Intermediate Similarity	NPD7874	Approved
0.7296	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6823	Phase 2
0.7289	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD943	Approved
0.7267	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7699	Phase 2
0.7263	Intermediate Similarity	NPD7700	Phase 2
0.7262	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3268	Approved
0.725	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8127	Discontinued
0.7231	Intermediate Similarity	NPD7584	Approved
0.7225	Intermediate Similarity	NPD6844	Discontinued
0.7216	Intermediate Similarity	NPD8319	Approved
0.7216	Intermediate Similarity	NPD8320	Phase 1
0.7215	Intermediate Similarity	NPD2798	Approved
0.7196	Intermediate Similarity	NPD6535	Approved
0.7196	Intermediate Similarity	NPD6534	Approved
0.7179	Intermediate Similarity	NPD1608	Approved
0.7158	Intermediate Similarity	NPD7685	Pre-registration
0.7158	Intermediate Similarity	NPD7240	Approved
0.7152	Intermediate Similarity	NPD1203	Approved
0.7152	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD1729	Discontinued
0.7143	Intermediate Similarity	NPD3764	Approved
0.7134	Intermediate Similarity	NPD4749	Approved
0.7134	Intermediate Similarity	NPD7097	Phase 1
0.7126	Intermediate Similarity	NPD7577	Discontinued
0.7126	Intermediate Similarity	NPD2654	Approved
0.7125	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7447	Phase 1
0.7117	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6355	Discontinued
0.7115	Intermediate Similarity	NPD1201	Approved
0.7108	Intermediate Similarity	NPD6005	Phase 3
0.7108	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6004	Phase 3
0.7108	Intermediate Similarity	NPD6003	Clinical (unspecified phase)

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