NPASS Compound

Structure

CID90497 OpenBabel06191715432D 50 56 0 0 1 0 0 0 0 0999 V2000 -1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7321 0.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 0.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7321 -1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2321 -2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2321 -0.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7321 0.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2321 -0.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 -1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7321 -1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2321 -0.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2321 -0.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2321 -2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2321 -0.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7321 -1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7321 -1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.7321 -1.2679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.4019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2321 -2.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7321 0.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 3 5 2 0 0 0 0 3 21 1 0 0 0 0 4 6 2 0 0 0 0 4 22 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 9 1 0 0 0 0 7 20 1 0 0 0 0 8 10 2 0 0 0 0 8 23 1 0 0 0 0 9 40 1 0 0 0 0 10 40 1 0 0 0 0 11 20 2 0 0 0 0 11 29 1 0 0 0 0 12 21 2 0 0 0 0 12 23 1 0 0 0 0 13 22 2 0 0 0 0 13 26 1 0 0 0 0 14 24 2 0 0 0 0 14 32 1 0 0 0 0 15 25 2 0 0 0 0 15 33 1 0 0 0 0 16 24 1 0 0 0 0 16 34 2 0 0 0 0 17 25 1 0 0 0 0 17 35 2 0 0 0 0 18 27 2 0 0 0 0 18 49 1 0 0 0 0 19 28 2 0 0 0 0 19 50 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 23 30 2 0 0 0 0 24 41 1 0 0 0 0 25 42 1 0 0 0 0 26 29 1 0 0 0 0 26 31 2 0 0 0 0 27 38 1 0 0 0 0 28 39 1 0 0 0 0 29 40 1 1 0 0 0 30 43 1 0 0 0 0 31 44 1 0 0 0 0 32 36 2 0 0 0 0 32 45 1 0 0 0 0 33 37 2 0 0 0 0 33 46 1 0 0 0 0 34 36 1 0 0 0 0 34 49 1 0 0 0 0 35 37 1 0 0 0 0 35 50 1 0 0 0 0 36 38 1 0 0 0 0 37 39 1 0 0 0 0 38 47 2 0 0 0 0 39 48 2 0 0 0 0 40 2 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	672.2
Volume:	680.947
LogP:	6.801
LogD:	2.798
LogS:	-3.218
# Rotatable Bonds:	5
TPSA:	181.8
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.098
Synthetic Accessibility Score:	4.434
Fsp3:	0.15
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:	-5.52
MDCK Permeability:	7.042584456939949e-06
Pgp-inhibitor:	0.193
Pgp-substrate:	0.374
Human Intestinal Absorption (HIA):	0.055
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	96.8448257446289%
Volume Distribution (VD):	0.417
Pgp-substrate:	2.611218214035034%

ADMET: Metabolism

CYP1A2-inhibitor:	0.814
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.932
CYP2C19-substrate:	0.034
CYP2C9-inhibitor:	0.682
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.35
CYP2D6-substrate:	0.317
CYP3A4-inhibitor:	0.38
CYP3A4-substrate:	0.073

ADMET: Excretion

Clearance (CL):	3.423
Half-life (T1/2):	0.346

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.125
Drug-inuced Liver Injury (DILI):	0.828
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.925
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.957
Carcinogencity:	0.113
Eye Corrosion:	0.003
Eye Irritation:	0.909
Respiratory Toxicity:	0.32

Download Data

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

Natural Product: NPC90497

Natural Product ID:	NPC90497
*Common Name:**	Mucusisoflavone A
IUPAC Name:	3-[3-[(E)-2-[(1S,2S)-2-[5-(5,7-dihydroxy-4-oxochromen-3-yl)-2-hydroxyphenyl]-1,4-dimethylcyclohex-3-en-1-yl]ethenyl]-4-hydroxyphenyl]-5,7-dihydroxychromen-4-one
Synonyms:	Mucusisoflavone A
Standard InCHIKey:	UXLMHNXEKOQLBQ-DCAFODOZSA-N
Standard InCHI:	InChI=1S/C40H32O10/c1-20-7-9-40(2,10-8-23-12-21(3-5-30(23)43)27-18-49-34-16-24(41)14-32(45)36(34)38(27)47)29(11-20)26-13-22(4-6-31(26)44)28-19-50-35-17-25(42)15-33(46)37(35)39(28)48/h3-6,8,10-19,29,41-46H,7,9H2,1-2H3/b10-8+/t29-,40+/m1/s1
SMILES:	Oc1cc(O)c2c(c1)occ(c2=O)c1ccc(c(c1)/C=C/[C@]1(C)CCC(=C[C@@H]1c1cc(ccc1O)c1coc2c(c1=O)c(O)cc(c2)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1812483
PubChem CID:	53344646
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002901] Isoflav-2-enes [CHEMONTID:0000494] Isoflavones

*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
NPO13906	Ficus mucuso	Species	Moraceae	Eukaryota	n.a.	fruit	n.a.	PMID[21619045]
NPO13906	Ficus mucuso	Species	Moraceae	Eukaryota	figs	Tongolo-Yaound, in the Central Region of Cameroon	2008-JUN	PMID[21619045]
NPO13906	Ficus mucuso	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14750	Usnea japonica	Species	Parmeliaceae	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
Others	2

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	98.7	%	PMID[526763]
NPT2	Others	Unspecified	IC50	=	680.0	nM	PMID[526763]
NPT2	Others	Unspecified	Ratio IC50	=	71.0	n.a.	PMID[526763]

☑ 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 NPC90497 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	426
0.1-0.2	1671
0.2-0.3	3524
0.3-0.4	9070
0.4-0.5	9979
0.5-0.6	4225
0.6-0.7	5879
0.7-0.8	5224
0.8-0.85	1917
0.85-0.9	639
0.9-0.95	137
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC324447
0.9477	High Similarity	NPC56049
0.9477	High Similarity	NPC54830
0.9419	High Similarity	NPC195136
0.9419	High Similarity	NPC121647
0.9412	High Similarity	NPC79375
0.9412	High Similarity	NPC37253
0.9408	High Similarity	NPC43345
0.94	High Similarity	NPC152233
0.9355	High Similarity	NPC105584
0.9342	High Similarity	NPC476552
0.9342	High Similarity	NPC476551
0.9342	High Similarity	NPC476553
0.9333	High Similarity	NPC475348
0.9333	High Similarity	NPC261271
0.929	High Similarity	NPC208258
0.9231	High Similarity	NPC15815
0.92	High Similarity	NPC471523
0.92	High Similarity	NPC471524
0.92	High Similarity	NPC282957
0.92	High Similarity	NPC471473
0.92	High Similarity	NPC194949
0.9172	High Similarity	NPC226462
0.9172	High Similarity	NPC98023
0.9167	High Similarity	NPC257166
0.9167	High Similarity	NPC1796
0.9161	High Similarity	NPC158027
0.9161	High Similarity	NPC100049
0.9161	High Similarity	NPC265624
0.9161	High Similarity	NPC205026
0.9161	High Similarity	NPC121649
0.9161	High Similarity	NPC248739
0.9161	High Similarity	NPC215203
0.9161	High Similarity	NPC186227
0.9161	High Similarity	NPC52611
0.9161	High Similarity	NPC150908
0.9161	High Similarity	NPC159707
0.9161	High Similarity	NPC14606
0.9125	High Similarity	NPC251336
0.9108	High Similarity	NPC51247
0.9097	High Similarity	NPC72425
0.9097	High Similarity	NPC71061
0.9097	High Similarity	NPC290830
0.9097	High Similarity	NPC121568
0.9097	High Similarity	NPC303485
0.9097	High Similarity	NPC194593
0.9073	High Similarity	NPC476055
0.9067	High Similarity	NPC297600
0.9051	High Similarity	NPC42965
0.9026	High Similarity	NPC188403
0.9	High Similarity	NPC26238
0.8987	High Similarity	NPC55443
0.8987	High Similarity	NPC18699
0.8981	High Similarity	NPC32867
0.8981	High Similarity	NPC192587
0.8968	High Similarity	NPC138299
0.8968	High Similarity	NPC222713
0.8968	High Similarity	NPC67322
0.8968	High Similarity	NPC178484
0.8968	High Similarity	NPC111112
0.8961	High Similarity	NPC291746
0.8961	High Similarity	NPC288840
0.8938	High Similarity	NPC473012
0.8933	High Similarity	NPC215311
0.8933	High Similarity	NPC172250
0.8933	High Similarity	NPC213659
0.8933	High Similarity	NPC265178
0.8933	High Similarity	NPC48624
0.8933	High Similarity	NPC259166
0.8933	High Similarity	NPC11056
0.8933	High Similarity	NPC144118
0.8933	High Similarity	NPC204985
0.8933	High Similarity	NPC80962
0.8933	High Similarity	NPC326109
0.8933	High Similarity	NPC219917
0.8924	High Similarity	NPC324358
0.8924	High Similarity	NPC322459
0.8924	High Similarity	NPC318527
0.8924	High Similarity	NPC323627
0.8924	High Similarity	NPC475184
0.8917	High Similarity	NPC182555
0.8917	High Similarity	NPC66441
0.891	High Similarity	NPC78324
0.891	High Similarity	NPC174086
0.891	High Similarity	NPC115601
0.891	High Similarity	NPC39154
0.891	High Similarity	NPC208011
0.8902	High Similarity	NPC477529
0.8889	High Similarity	NPC25844
0.8882	High Similarity	NPC469395
0.8882	High Similarity	NPC473009
0.8875	High Similarity	NPC189552
0.8875	High Similarity	NPC61382
0.8875	High Similarity	NPC273467
0.8875	High Similarity	NPC312273
0.8875	High Similarity	NPC103816
0.8875	High Similarity	NPC301256
0.8874	High Similarity	NPC268204
0.8874	High Similarity	NPC55832
0.8874	High Similarity	NPC232021
0.8874	High Similarity	NPC40118
0.8874	High Similarity	NPC469404
0.8874	High Similarity	NPC26051
0.8874	High Similarity	NPC126534
0.8874	High Similarity	NPC52789
0.8868	High Similarity	NPC51760
0.8868	High Similarity	NPC295090
0.8867	High Similarity	NPC295384
0.8867	High Similarity	NPC283429
0.8861	High Similarity	NPC69531
0.8839	High Similarity	NPC3642
0.8834	High Similarity	NPC253730
0.8834	High Similarity	NPC286230
0.8831	High Similarity	NPC97716
0.8831	High Similarity	NPC24673
0.8831	High Similarity	NPC79469
0.8831	High Similarity	NPC237635
0.8831	High Similarity	NPC201731
0.8831	High Similarity	NPC104406
0.8827	High Similarity	NPC473010
0.8827	High Similarity	NPC469664
0.8812	High Similarity	NPC470342
0.8812	High Similarity	NPC312993
0.8812	High Similarity	NPC472060
0.8812	High Similarity	NPC186325
0.8812	High Similarity	NPC472052
0.8808	High Similarity	NPC101366
0.8808	High Similarity	NPC253822
0.8805	High Similarity	NPC271741
0.8805	High Similarity	NPC287789
0.88	High Similarity	NPC243528
0.88	High Similarity	NPC251681
0.8797	High Similarity	NPC254351
0.8797	High Similarity	NPC226656
0.8797	High Similarity	NPC134171
0.8797	High Similarity	NPC66508
0.8797	High Similarity	NPC300668
0.8774	High Similarity	NPC6511
0.8774	High Similarity	NPC122894
0.8774	High Similarity	NPC266572
0.8773	High Similarity	NPC120857
0.8773	High Similarity	NPC17274
0.8773	High Similarity	NPC85047
0.8766	High Similarity	NPC110882
0.8766	High Similarity	NPC271944
0.8766	High Similarity	NPC85393
0.8766	High Similarity	NPC476088
0.8766	High Similarity	NPC474161
0.8758	High Similarity	NPC11700
0.8758	High Similarity	NPC476178
0.8758	High Similarity	NPC472261
0.8758	High Similarity	NPC117836
0.8758	High Similarity	NPC475705
0.8758	High Similarity	NPC51887
0.875	High Similarity	NPC177650
0.875	High Similarity	NPC324736
0.8742	High Similarity	NPC61112
0.8742	High Similarity	NPC198489
0.8742	High Similarity	NPC477956
0.8742	High Similarity	NPC309648
0.8733	High Similarity	NPC322301
0.8733	High Similarity	NPC23870
0.8733	High Similarity	NPC255801
0.8733	High Similarity	NPC181124
0.8733	High Similarity	NPC162680
0.8733	High Similarity	NPC116632
0.8733	High Similarity	NPC303644
0.8733	High Similarity	NPC7013
0.8733	High Similarity	NPC209560
0.8733	High Similarity	NPC294409
0.8733	High Similarity	NPC153979
0.8726	High Similarity	NPC305965
0.8718	High Similarity	NPC132345
0.8718	High Similarity	NPC471114
0.8712	High Similarity	NPC169471
0.871	High Similarity	NPC10990
0.871	High Similarity	NPC300988
0.8701	High Similarity	NPC257236
0.8701	High Similarity	NPC319752
0.8701	High Similarity	NPC328623
0.8701	High Similarity	NPC271288
0.8701	High Similarity	NPC278175
0.8696	High Similarity	NPC472618
0.8679	High Similarity	NPC258474
0.8679	High Similarity	NPC201227
0.8675	High Similarity	NPC55162
0.8675	High Similarity	NPC12175
0.8675	High Similarity	NPC477055
0.8675	High Similarity	NPC278323
0.8675	High Similarity	NPC477056
0.8675	High Similarity	NPC90665
0.8675	High Similarity	NPC309154
0.8675	High Similarity	NPC279668
0.8675	High Similarity	NPC21350
0.8667	High Similarity	NPC24394
0.8667	High Similarity	NPC213603
0.8667	High Similarity	NPC249606
0.8667	High Similarity	NPC274109
0.8667	High Similarity	NPC12165
0.8667	High Similarity	NPC66349

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 NPC90497 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	999
0.2-0.3	1524
0.3-0.4	2662
0.4-0.5	2074
0.5-0.6	1013
0.6-0.7	339
0.7-0.8	123
0.8-0.85	26
0.85-0.9	9
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8917	High Similarity	NPD8443	Clinical (unspecified phase)
0.8712	High Similarity	NPD7852	Clinical (unspecified phase)
0.8701	High Similarity	NPD7410	Clinical (unspecified phase)
0.8625	High Similarity	NPD7768	Phase 2
0.86	High Similarity	NPD1510	Phase 2
0.8544	High Similarity	NPD4380	Phase 2
0.8528	High Similarity	NPD6959	Discontinued
0.8491	Intermediate Similarity	NPD7411	Suspended
0.8462	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD7819	Suspended
0.8344	Intermediate Similarity	NPD1607	Approved
0.8344	Intermediate Similarity	NPD6651	Approved
0.8333	Intermediate Similarity	NPD1240	Approved
0.8232	Intermediate Similarity	NPD7075	Discontinued
0.8214	Intermediate Similarity	NPD7473	Discontinued
0.8194	Intermediate Similarity	NPD1549	Phase 2
0.8182	Intermediate Similarity	NPD2796	Approved
0.8165	Intermediate Similarity	NPD7390	Discontinued
0.8137	Intermediate Similarity	NPD7458	Discontinued
0.8129	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6232	Discontinued
0.8012	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6801	Discontinued
0.7975	Intermediate Similarity	NPD6599	Discontinued
0.7975	Intermediate Similarity	NPD7003	Approved
0.7975	Intermediate Similarity	NPD3750	Approved
0.7941	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6166	Phase 2
0.7911	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD2800	Approved
0.7904	Intermediate Similarity	NPD3749	Approved
0.7848	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1934	Approved
0.7765	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD2801	Approved
0.7722	Intermediate Similarity	NPD2935	Discontinued
0.7716	Intermediate Similarity	NPD1511	Approved
0.7716	Intermediate Similarity	NPD6799	Approved
0.7706	Intermediate Similarity	NPD5494	Approved
0.7701	Intermediate Similarity	NPD7054	Approved
0.7684	Intermediate Similarity	NPD8313	Approved
0.7684	Intermediate Similarity	NPD8312	Approved
0.7683	Intermediate Similarity	NPD5403	Approved
0.768	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2533	Approved
0.7669	Intermediate Similarity	NPD2534	Approved
0.7669	Intermediate Similarity	NPD2532	Approved
0.7658	Intermediate Similarity	NPD3748	Approved
0.7657	Intermediate Similarity	NPD7074	Phase 3
0.7657	Intermediate Similarity	NPD7472	Approved
0.764	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3882	Suspended
0.7633	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7808	Phase 3
0.7622	Intermediate Similarity	NPD1512	Approved
0.7614	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1551	Phase 2
0.761	Intermediate Similarity	NPD5408	Approved
0.761	Intermediate Similarity	NPD5406	Approved
0.761	Intermediate Similarity	NPD5405	Approved
0.761	Intermediate Similarity	NPD6100	Approved
0.761	Intermediate Similarity	NPD5404	Approved
0.761	Intermediate Similarity	NPD6099	Approved
0.76	Intermediate Similarity	NPD5844	Phase 1
0.7597	Intermediate Similarity	NPD4908	Phase 1
0.7582	Intermediate Similarity	NPD2798	Approved
0.7574	Intermediate Similarity	NPD3817	Phase 2
0.7571	Intermediate Similarity	NPD7251	Discontinued
0.7571	Intermediate Similarity	NPD6559	Discontinued
0.7561	Intermediate Similarity	NPD5401	Approved
0.7547	Intermediate Similarity	NPD2799	Discontinued
0.7543	Intermediate Similarity	NPD3818	Discontinued
0.7531	Intermediate Similarity	NPD4628	Phase 3
0.7514	Intermediate Similarity	NPD6797	Phase 2
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.7514	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3226	Approved
0.7471	Intermediate Similarity	NPD5402	Approved
0.747	Intermediate Similarity	NPD920	Approved
0.7469	Intermediate Similarity	NPD1243	Approved
0.7455	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2344	Approved
0.7439	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3972	Approved
0.7401	Intermediate Similarity	NPD7286	Phase 2
0.7365	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD8150	Discontinued
0.7358	Intermediate Similarity	NPD8151	Discontinued
0.7349	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7871	Phase 2
0.733	Intermediate Similarity	NPD7870	Phase 2
0.7317	Intermediate Similarity	NPD8166	Discontinued
0.7312	Intermediate Similarity	NPD4360	Phase 2
0.7312	Intermediate Similarity	NPD4363	Phase 3
0.731	Intermediate Similarity	NPD8455	Phase 2
0.7296	Intermediate Similarity	NPD943	Approved
0.7278	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2313	Discontinued
0.7277	Intermediate Similarity	NPD7698	Approved
0.7277	Intermediate Similarity	NPD7697	Approved
0.7277	Intermediate Similarity	NPD7696	Phase 3
0.7273	Intermediate Similarity	NPD2309	Approved
0.7268	Intermediate Similarity	NPD8434	Phase 2
0.7261	Intermediate Similarity	NPD6832	Phase 2
0.7238	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6780	Approved
0.7211	Intermediate Similarity	NPD6777	Approved
0.7211	Intermediate Similarity	NPD6776	Approved
0.7211	Intermediate Similarity	NPD6779	Approved
0.7211	Intermediate Similarity	NPD6781	Approved
0.7211	Intermediate Similarity	NPD6778	Approved
0.7211	Intermediate Similarity	NPD6782	Approved
0.7202	Intermediate Similarity	NPD6273	Approved
0.7188	Intermediate Similarity	NPD7435	Discontinued
0.7181	Intermediate Similarity	NPD4361	Phase 2
0.7181	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1470	Approved
0.7175	Intermediate Similarity	NPD3926	Phase 2
0.717	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3268	Approved
0.7151	Intermediate Similarity	NPD7177	Discontinued
0.7143	Intermediate Similarity	NPD919	Approved
0.7143	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1201	Approved
0.7143	Intermediate Similarity	NPD1610	Phase 2
0.7134	Intermediate Similarity	NPD2346	Discontinued
0.7134	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7701	Phase 2
0.712	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5710	Approved
0.7119	Intermediate Similarity	NPD5711	Approved
0.7119	Intermediate Similarity	NPD7229	Phase 3
0.711	Intermediate Similarity	NPD5761	Phase 2
0.711	Intermediate Similarity	NPD5760	Phase 2
0.7107	Intermediate Similarity	NPD7801	Approved
0.707	Intermediate Similarity	NPD2797	Approved
0.707	Intermediate Similarity	NPD1203	Approved
0.7069	Intermediate Similarity	NPD4288	Approved
0.7063	Intermediate Similarity	NPD3764	Approved
0.7062	Intermediate Similarity	NPD1247	Approved
0.7056	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7874	Approved
0.7056	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD37	Approved
0.7048	Intermediate Similarity	NPD2654	Approved
0.7047	Intermediate Similarity	NPD6823	Phase 2
0.7039	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7700	Phase 2
0.7016	Intermediate Similarity	NPD7699	Phase 2
0.7012	Intermediate Similarity	NPD7033	Discontinued
0.7012	Intermediate Similarity	NPD4308	Phase 3
0.7011	Intermediate Similarity	NPD1465	Phase 2
0.7005	Intermediate Similarity	NPD4287	Approved
0.6994	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1548	Phase 1
0.699	Remote Similarity	NPD7584	Approved
0.6983	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD8320	Phase 1
0.6974	Remote Similarity	NPD8319	Approved
0.6971	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7199	Phase 2
0.6966	Remote Similarity	NPD8127	Discontinued
0.6962	Remote Similarity	NPD1164	Approved
0.6961	Remote Similarity	NPD7228	Approved
0.6961	Remote Similarity	NPD3751	Discontinued
0.6954	Remote Similarity	NPD7577	Discontinued
0.6949	Remote Similarity	NPD6234	Discontinued
0.6948	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6534	Approved
0.6947	Remote Similarity	NPD6535	Approved
0.6941	Remote Similarity	NPD7447	Phase 1
0.6935	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7783	Phase 2
0.6932	Remote Similarity	NPD4965	Approved
0.6932	Remote Similarity	NPD4967	Phase 2
0.6932	Remote Similarity	NPD4966	Approved
0.6928	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD6104	Discontinued
0.6899	Remote Similarity	NPD1876	Approved
0.6899	Remote Similarity	NPD3225	Approved
0.6894	Remote Similarity	NPD4625	Phase 3
0.6889	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD1729	Discontinued
0.6883	Remote Similarity	NPD9545	Approved
0.6882	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD9717	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