NPASS Compound

Structure

NPC471473 OpenBabel07101718242D 39 42 0 0 1 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 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 3.4641 -1.0000 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 -2.5981 -5.5000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 3 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 4.3301 -1.5000 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 -2.5981 -4.5000 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 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 -3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 38 1 0 0 0 0 2 39 1 0 0 0 0 3 10 1 0 0 0 0 3 20 2 0 0 0 0 4 11 2 0 0 0 0 4 20 1 0 0 0 0 5 12 1 0 0 0 0 5 21 2 0 0 0 0 6 13 2 0 0 0 0 6 21 1 0 0 0 0 7 14 2 0 0 0 0 7 22 1 0 0 0 0 8 15 1 0 0 0 0 8 22 1 0 0 0 0 9 16 1 0 0 0 0 9 23 1 0 0 0 0 10 24 2 0 0 0 0 11 24 1 0 0 0 0 12 25 2 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 29 1 0 0 0 0 17 23 1 0 0 0 0 17 28 2 0 0 0 0 18 26 2 0 0 0 0 18 31 1 0 0 0 0 19 30 2 0 0 0 0 19 32 1 0 0 0 0 20 27 1 0 0 0 0 21 29 1 0 0 0 0 22 31 2 0 0 0 0 23 32 2 0 0 0 0 24 33 1 0 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 27 28 1 0 0 0 0 28 30 1 0 0 0 0 29 36 2 0 0 0 0 30 37 1 0 0 0 0 31 38 1 0 0 0 0 32 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.21
Volume:	555.06
LogP:	4.975
LogD:	4.037
LogS:	-3.655
# Rotatable Bonds:	11
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.174
Synthetic Accessibility Score:	3.116
Fsp3:	0.219
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.215
MDCK Permeability:	9.644540114095435e-06
Pgp-inhibitor:	0.496
Pgp-substrate:	0.141
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	99.3565444946289%
Volume Distribution (VD):	0.499
Pgp-substrate:	0.8355116248130798%

ADMET: Metabolism

CYP1A2-inhibitor:	0.458
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.956
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.919
CYP2C9-substrate:	0.985
CYP2D6-inhibitor:	0.833
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.87
CYP3A4-substrate:	0.751

ADMET: Excretion

Clearance (CL):	9.596
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.181
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.088
AMES Toxicity:	0.231
Rat Oral Acute Toxicity:	0.562
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.915
Carcinogencity:	0.099
Eye Corrosion:	0.003
Eye Irritation:	0.641
Respiratory Toxicity:	0.066

Download Data

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

Natural Product: NPC471473

Natural Product ID:	NPC471473
*Common Name:**	1-[5-(2-Methoxy-4,4-Dihydroxydihydrochalconyl)]-1-(4-Hydroxyphenyl)-3-(2-Methoxy-4-Hydroxyphenyl)Propane
IUPAC Name:	3-[4-hydroxy-5-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-methoxyphenyl]-1-(4-hydroxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	KJDKNNNKRLAENJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H32O7/c1-38-31-18-26(35)14-7-22(31)8-15-27(20-3-10-24(33)11-4-20)28-17-23(32(39-2)19-30(28)37)9-16-29(36)21-5-12-25(34)13-6-21/h3-7,10-14,17-19,27,33-35,37H,8-9,15-16H2,1-2H3
SMILES:	COc1cc(O)c(cc1CCC(=O)c1ccc(cc1)O)C(c1ccc(cc1)O)CCc1ccc(cc1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251977
PubChem CID:	44445075
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12016928]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	stems	Ningming County, Guangxi autonomous region, China	2006-Jan	PMID[17883259]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21661731]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
MIC	1

Activity Type	# Activity
Individual Protein	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1592	Individual Protein	Dipeptidyl peptidase IV	Homo sapiens	IC50	>	36900.0	nM	PMID[522271]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	60600.0	nM	PMID[522271]
NPT670	Individual Protein	Thrombin	Homo sapiens	IC50	=	26300.0	nM	PMID[522271]

☑ 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 NPC471473 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	378
0.1-0.2	1547
0.2-0.3	3526
0.3-0.4	9277
0.4-0.5	9302
0.5-0.6	3518
0.6-0.7	6138
0.7-0.8	6581
0.8-0.85	1575
0.85-0.9	756
0.9-0.95	89
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471523
1.0	High Similarity	NPC471524
0.9787	High Similarity	NPC152233
0.9716	High Similarity	NPC261271
0.9716	High Similarity	NPC475348
0.9583	High Similarity	NPC476551
0.9583	High Similarity	NPC476553
0.9583	High Similarity	NPC476552
0.9517	High Similarity	NPC43345
0.9452	High Similarity	NPC324447
0.9437	High Similarity	NPC194949
0.9437	High Similarity	NPC282957
0.942	High Similarity	NPC24394
0.9388	High Similarity	NPC37253
0.9388	High Similarity	NPC79375
0.9362	High Similarity	NPC26238
0.9262	High Similarity	NPC208258
0.9236	High Similarity	NPC25844
0.9214	High Similarity	NPC23870
0.9203	High Similarity	NPC27643
0.92	High Similarity	NPC15815
0.92	High Similarity	NPC90497
0.9195	High Similarity	NPC56049
0.9195	High Similarity	NPC54830
0.9189	High Similarity	NPC121568
0.9184	High Similarity	NPC178484
0.9161	High Similarity	NPC297600
0.9149	High Similarity	NPC251681
0.9149	High Similarity	NPC243528
0.9139	High Similarity	NPC226462
0.9139	High Similarity	NPC195136
0.9139	High Similarity	NPC121647
0.9139	High Similarity	NPC98023
0.9133	High Similarity	NPC257166
0.9133	High Similarity	NPC1796
0.9085	High Similarity	NPC477956
0.9078	High Similarity	NPC153979
0.9073	High Similarity	NPC105584
0.9073	High Similarity	NPC51247
0.9058	High Similarity	NPC66384
0.9058	High Similarity	NPC164236
0.9058	High Similarity	NPC309717
0.9058	High Similarity	NPC189106
0.9058	High Similarity	NPC128348
0.9058	High Similarity	NPC112192
0.9021	High Similarity	NPC259166
0.9021	High Similarity	NPC48624
0.9021	High Similarity	NPC172250
0.9021	High Similarity	NPC215311
0.9021	High Similarity	NPC204985
0.9021	High Similarity	NPC213659
0.9021	High Similarity	NPC265178
0.9021	High Similarity	NPC80962
0.9021	High Similarity	NPC326109
0.9021	High Similarity	NPC219917
0.9021	High Similarity	NPC144118
0.9021	High Similarity	NPC11056
0.9014	High Similarity	NPC21350
0.9013	High Similarity	NPC42965
0.9007	High Similarity	NPC249606
0.9007	High Similarity	NPC1486
0.9007	High Similarity	NPC12165
0.9007	High Similarity	NPC274109
0.9007	High Similarity	NPC186838
0.9007	High Similarity	NPC213603
0.9007	High Similarity	NPC168105
0.9007	High Similarity	NPC66349
0.9007	High Similarity	NPC150399
0.9007	High Similarity	NPC477242
0.9007	High Similarity	NPC41461
0.9007	High Similarity	NPC25287
0.9007	High Similarity	NPC477243
0.9007	High Similarity	NPC477244
0.9007	High Similarity	NPC98115
0.9	High Similarity	NPC158027
0.9	High Similarity	NPC248739
0.9	High Similarity	NPC52611
0.9	High Similarity	NPC186227
0.9	High Similarity	NPC14606
0.9	High Similarity	NPC215203
0.9	High Similarity	NPC100049
0.9	High Similarity	NPC205026
0.9	High Similarity	NPC150908
0.9	High Similarity	NPC265624
0.9	High Similarity	NPC121649
0.9	High Similarity	NPC159707
0.8973	High Similarity	NPC477955
0.8958	High Similarity	NPC232021
0.8958	High Similarity	NPC40118
0.8958	High Similarity	NPC55832
0.8958	High Similarity	NPC469404
0.8958	High Similarity	NPC126534
0.8958	High Similarity	NPC26051
0.8958	High Similarity	NPC52789
0.8958	High Similarity	NPC268204
0.8951	High Similarity	NPC472366
0.8951	High Similarity	NPC283429
0.8951	High Similarity	NPC295384
0.8944	High Similarity	NPC317119
0.8944	High Similarity	NPC255801
0.8944	High Similarity	NPC472419
0.8944	High Similarity	NPC322301
0.8936	High Similarity	NPC13575
0.8936	High Similarity	NPC156092
0.8936	High Similarity	NPC131039
0.8933	High Similarity	NPC71061
0.8933	High Similarity	NPC303485
0.8933	High Similarity	NPC290830
0.8933	High Similarity	NPC194593
0.8933	High Similarity	NPC72425
0.8919	High Similarity	NPC3642
0.8913	High Similarity	NPC247779
0.8904	High Similarity	NPC271288
0.8904	High Similarity	NPC328623
0.8904	High Similarity	NPC476055
0.8896	High Similarity	NPC473012
0.8889	High Similarity	NPC253822
0.8889	High Similarity	NPC101366
0.8882	High Similarity	NPC475184
0.8882	High Similarity	NPC318527
0.8882	High Similarity	NPC324358
0.8882	High Similarity	NPC322459
0.8882	High Similarity	NPC323627
0.8881	High Similarity	NPC472368
0.8874	High Similarity	NPC226656
0.8874	High Similarity	NPC66508
0.8867	High Similarity	NPC39154
0.8867	High Similarity	NPC208011
0.8867	High Similarity	NPC115601
0.8867	High Similarity	NPC78324
0.8865	High Similarity	NPC286336
0.8865	High Similarity	NPC103842
0.8851	High Similarity	NPC145467
0.8851	High Similarity	NPC472841
0.8851	High Similarity	NPC39195
0.8851	High Similarity	NPC122894
0.8846	High Similarity	NPC251336
0.8844	High Similarity	NPC109183
0.8844	High Similarity	NPC473078
0.8844	High Similarity	NPC470132
0.8844	High Similarity	NPC470131
0.8844	High Similarity	NPC470134
0.8844	High Similarity	NPC470133
0.8839	High Similarity	NPC473009
0.8836	High Similarity	NPC166138
0.8836	High Similarity	NPC18585
0.8836	High Similarity	NPC51887
0.8836	High Similarity	NPC106985
0.8836	High Similarity	NPC476178
0.8836	High Similarity	NPC475705
0.8836	High Similarity	NPC117836
0.8831	High Similarity	NPC301256
0.8831	High Similarity	NPC312273
0.8828	High Similarity	NPC110969
0.8828	High Similarity	NPC282300
0.8828	High Similarity	NPC14871
0.8828	High Similarity	NPC321980
0.8828	High Similarity	NPC470087
0.8828	High Similarity	NPC470089
0.8824	High Similarity	NPC18699
0.8824	High Similarity	NPC55443
0.8819	High Similarity	NPC470211
0.8816	High Similarity	NPC192587
0.8816	High Similarity	NPC32867
0.8816	High Similarity	NPC69531
0.8811	High Similarity	NPC181124
0.8811	High Similarity	NPC294409
0.8811	High Similarity	NPC209560
0.8811	High Similarity	NPC7013
0.8811	High Similarity	NPC116632
0.8811	High Similarity	NPC303644
0.8811	High Similarity	NPC162680
0.88	High Similarity	NPC316960
0.88	High Similarity	NPC309512
0.88	High Similarity	NPC138299
0.88	High Similarity	NPC305965
0.88	High Similarity	NPC111112
0.88	High Similarity	NPC67322
0.88	High Similarity	NPC148945
0.88	High Similarity	NPC78835
0.88	High Similarity	NPC317715
0.88	High Similarity	NPC204561
0.88	High Similarity	NPC222713
0.8794	High Similarity	NPC312318
0.8794	High Similarity	NPC159623
0.8794	High Similarity	NPC56031
0.8794	High Similarity	NPC263670
0.8794	High Similarity	NPC472365
0.8794	High Similarity	NPC82225
0.8794	High Similarity	NPC20560
0.8794	High Similarity	NPC28753
0.8794	High Similarity	NPC188646
0.8794	High Similarity	NPC242294
0.8794	High Similarity	NPC144051
0.8794	High Similarity	NPC139813
0.8794	High Similarity	NPC337373
0.8794	High Similarity	NPC192304
0.8794	High Similarity	NPC204960
0.8794	High Similarity	NPC175098
0.8794	High Similarity	NPC294593

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 NPC471473 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	962
0.2-0.3	1334
0.3-0.4	2531
0.4-0.5	2068
0.5-0.6	1239
0.6-0.7	481
0.7-0.8	154
0.8-0.85	23
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD8443	Clinical (unspecified phase)
0.8816	High Similarity	NPD7768	Phase 2
0.8776	High Similarity	NPD7410	Clinical (unspecified phase)
0.8671	High Similarity	NPD1510	Phase 2
0.8662	High Similarity	NPD7852	Clinical (unspecified phase)
0.8652	High Similarity	NPD1240	Approved
0.8649	High Similarity	NPD4378	Clinical (unspecified phase)
0.8553	High Similarity	NPD7411	Suspended
0.8531	High Similarity	NPD1607	Approved
0.8487	Intermediate Similarity	NPD4380	Phase 2
0.8442	Intermediate Similarity	NPD7819	Suspended
0.8435	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD3750	Approved
0.8367	Intermediate Similarity	NPD1549	Phase 2
0.8354	Intermediate Similarity	NPD6959	Discontinued
0.8299	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD7075	Discontinued
0.8261	Intermediate Similarity	NPD7473	Discontinued
0.8252	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD2796	Approved
0.8205	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7458	Discontinued
0.8165	Intermediate Similarity	NPD3749	Approved
0.8151	Intermediate Similarity	NPD6651	Approved
0.8133	Intermediate Similarity	NPD7003	Approved
0.8112	Intermediate Similarity	NPD4908	Phase 1
0.8092	Intermediate Similarity	NPD7390	Discontinued
0.8075	Intermediate Similarity	NPD6232	Discontinued
0.8041	Intermediate Similarity	NPD3748	Approved
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7939	Intermediate Similarity	NPD5844	Phase 1
0.7939	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6801	Discontinued
0.7911	Intermediate Similarity	NPD1934	Approved
0.7867	Intermediate Similarity	NPD6099	Approved
0.7867	Intermediate Similarity	NPD6100	Approved
0.7866	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6166	Phase 2
0.7862	Intermediate Similarity	NPD2801	Approved
0.7857	Intermediate Similarity	NPD1511	Approved
0.7857	Intermediate Similarity	NPD6799	Approved
0.7844	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD5494	Approved
0.7829	Intermediate Similarity	NPD2800	Approved
0.7821	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD2799	Discontinued
0.7785	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3882	Suspended
0.7756	Intermediate Similarity	NPD1512	Approved
0.7748	Intermediate Similarity	NPD5404	Approved
0.7748	Intermediate Similarity	NPD5406	Approved
0.7748	Intermediate Similarity	NPD5408	Approved
0.7748	Intermediate Similarity	NPD5405	Approved
0.7724	Intermediate Similarity	NPD2798	Approved
0.7697	Intermediate Similarity	NPD2344	Approved
0.7692	Intermediate Similarity	NPD2533	Approved
0.7692	Intermediate Similarity	NPD2534	Approved
0.7692	Intermediate Similarity	NPD2532	Approved
0.7692	Intermediate Similarity	NPD3972	Approved
0.7662	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD3268	Approved
0.7635	Intermediate Similarity	NPD3764	Approved
0.7632	Intermediate Similarity	NPD1551	Phase 2
0.7622	Intermediate Similarity	NPD1610	Phase 2
0.761	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1243	Approved
0.758	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7074	Phase 3
0.7534	Intermediate Similarity	NPD2797	Approved
0.7533	Intermediate Similarity	NPD943	Approved
0.7531	Intermediate Similarity	NPD8455	Phase 2
0.753	Intermediate Similarity	NPD7229	Phase 3
0.7529	Intermediate Similarity	NPD5953	Discontinued
0.7515	Intermediate Similarity	NPD7054	Approved
0.7515	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD8313	Approved
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6559	Discontinued
0.7485	Intermediate Similarity	NPD3817	Phase 2
0.7484	Intermediate Similarity	NPD5403	Approved
0.7484	Intermediate Similarity	NPD920	Approved
0.7471	Intermediate Similarity	NPD7472	Approved
0.7466	Intermediate Similarity	NPD1876	Approved
0.7456	Intermediate Similarity	NPD3818	Discontinued
0.7456	Intermediate Similarity	NPD7177	Discontinued
0.7452	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7808	Phase 3
0.743	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1465	Phase 2
0.7407	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2313	Discontinued
0.7384	Intermediate Similarity	NPD7251	Discontinued
0.7378	Intermediate Similarity	NPD4288	Approved
0.7368	Intermediate Similarity	NPD5124	Phase 1
0.7368	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7577	Discontinued
0.7358	Intermediate Similarity	NPD5401	Approved
0.7358	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1548	Phase 1
0.7343	Intermediate Similarity	NPD9545	Approved
0.7338	Intermediate Similarity	NPD4308	Phase 3
0.7333	Intermediate Similarity	NPD4625	Phase 3
0.7329	Intermediate Similarity	NPD1608	Approved
0.7326	Intermediate Similarity	NPD6797	Phase 2
0.7318	Intermediate Similarity	NPD4363	Phase 3
0.7318	Intermediate Similarity	NPD4360	Phase 2
0.7314	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6273	Approved
0.7297	Intermediate Similarity	NPD1470	Approved
0.7297	Intermediate Similarity	NPD3266	Approved
0.7297	Intermediate Similarity	NPD1203	Approved
0.7297	Intermediate Similarity	NPD3267	Approved
0.7292	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3926	Phase 2
0.7273	Intermediate Similarity	NPD5402	Approved
0.7267	Intermediate Similarity	NPD6832	Phase 2
0.7262	Intermediate Similarity	NPD7199	Phase 2
0.7261	Intermediate Similarity	NPD2654	Approved
0.726	Intermediate Similarity	NPD1201	Approved
0.726	Intermediate Similarity	NPD422	Phase 1
0.7256	Intermediate Similarity	NPD37	Approved
0.7255	Intermediate Similarity	NPD230	Phase 1
0.725	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2346	Discontinued
0.723	Intermediate Similarity	NPD3225	Approved
0.723	Intermediate Similarity	NPD1283	Approved
0.7215	Intermediate Similarity	NPD8166	Discontinued
0.7191	Intermediate Similarity	NPD4287	Approved
0.7182	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4361	Phase 2
0.7181	Intermediate Similarity	NPD8151	Discontinued
0.7181	Intermediate Similarity	NPD1164	Approved
0.7176	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1651	Approved
0.7171	Intermediate Similarity	NPD6798	Discontinued
0.7171	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4749	Approved
0.7162	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7870	Phase 2
0.7151	Intermediate Similarity	NPD7871	Phase 2
0.7143	Intermediate Similarity	NPD7447	Phase 1
0.7143	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD919	Approved
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4967	Phase 2
0.7126	Intermediate Similarity	NPD4965	Approved
0.7126	Intermediate Similarity	NPD4966	Approved
0.7123	Intermediate Similarity	NPD17	Approved
0.7118	Intermediate Similarity	NPD5711	Approved
0.7118	Intermediate Similarity	NPD5710	Approved
0.7115	Intermediate Similarity	NPD7033	Discontinued
0.7105	Intermediate Similarity	NPD3027	Phase 3
0.7097	Intermediate Similarity	NPD7698	Approved
0.7097	Intermediate Similarity	NPD7697	Approved
0.7097	Intermediate Similarity	NPD7696	Phase 3
0.7095	Intermediate Similarity	NPD9717	Approved
0.7083	Intermediate Similarity	NPD9493	Approved
0.7083	Intermediate Similarity	NPD6971	Discontinued
0.7083	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8150	Discontinued
0.7078	Intermediate Similarity	NPD4307	Phase 2
0.7076	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1247	Approved
0.7052	Intermediate Similarity	NPD7228	Approved
0.7052	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6782	Approved
0.7027	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6781	Approved
0.7027	Intermediate Similarity	NPD1281	Approved
0.7027	Intermediate Similarity	NPD6780	Approved
0.7027	Intermediate Similarity	NPD6778	Approved
0.7027	Intermediate Similarity	NPD6777	Approved
0.7027	Intermediate Similarity	NPD6779	Approved
0.7027	Intermediate Similarity	NPD6776	Approved
0.7019	Intermediate Similarity	NPD7440	Discontinued
0.7007	Intermediate Similarity	NPD4626	Approved
0.7006	Intermediate Similarity	NPD5761	Phase 2
0.7006	Intermediate Similarity	NPD651	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