NPASS Compound

Structure

NPC306267 OpenBabel07101719142D 41 47 0 0 1 0 0 0 0 0999 V2000 4.2399 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 -1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 -1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 4.4062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 -1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 1.4687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6960 1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3919 0.9792 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5439 2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8480 0.4896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2399 -1.4687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 3.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 4.4062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 -1.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 4.4062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 0.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 1.4687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 0.9792 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 6 2 0 0 0 0 1 12 1 0 0 0 0 2 4 1 0 0 0 0 2 13 2 0 0 0 0 3 5 2 0 0 0 0 3 13 1 0 0 0 0 4 14 2 0 0 0 0 5 14 1 0 0 0 0 6 17 1 0 0 0 0 7 12 2 0 0 0 0 7 19 1 0 0 0 0 8 15 2 0 0 0 0 8 20 1 0 0 0 0 9 15 1 0 0 0 0 9 23 2 0 0 0 0 10 16 1 0 0 0 0 10 22 1 0 0 0 0 11 18 2 0 0 0 0 11 21 1 0 0 0 0 14 31 1 0 0 0 0 15 32 1 0 0 0 0 16 18 1 0 0 0 0 16 28 2 0 0 0 0 17 19 2 0 0 0 0 17 33 1 0 0 0 0 18 34 1 0 0 0 0 19 35 1 0 0 0 0 20 24 2 0 0 0 0 20 36 1 0 0 0 0 21 25 2 0 0 0 0 21 37 1 0 0 0 0 22 27 1 0 0 0 0 22 38 1 1 0 0 0 23 24 1 0 0 0 0 23 40 1 0 0 0 0 24 26 1 0 0 0 0 25 28 1 0 0 0 0 26 25 1 1 0 0 0 26 29 1 0 0 0 0 27 12 1 1 0 0 0 27 39 1 0 0 0 0 28 39 1 0 0 0 0 29 30 1 1 0 0 0 29 41 1 0 0 0 0 30 13 1 1 0 0 0 30 40 1 0 0 0 0 30 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.13
Volume:	532.596
LogP:	3.491
LogD:	2.457
LogS:	-3.73
# Rotatable Bonds:	3
TPSA:	192.83
# H-Bond Aceptor:	11
# H-Bond Donor:	8
# Rings:	7
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.135
Synthetic Accessibility Score:	4.662
Fsp3:	0.2
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.673
MDCK Permeability:	5.007228082831716e-06
Pgp-inhibitor:	0.038
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.962
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	91.43724822998047%
Volume Distribution (VD):	0.376
Pgp-substrate:	5.940118789672852%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.664
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.225
CYP3A4-inhibitor:	0.145
CYP3A4-substrate:	0.339

ADMET: Excretion

Clearance (CL):	10.824
Half-life (T1/2):	0.723

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.878
AMES Toxicity:	0.612
Rat Oral Acute Toxicity:	0.676
Maximum Recommended Daily Dose:	0.392
Skin Sensitization:	0.97
Carcinogencity:	0.26
Eye Corrosion:	0.003
Eye Irritation:	0.925
Respiratory Toxicity:	0.054

Download Data

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

Natural Product: NPC306267

Natural Product ID:	NPC306267
*Common Name:**	2Beta,3Beta-Epoxy-5,7,4'-Trihydroxyflavan-(4Alpha->8)-Epicatechin
IUPAC Name:	(2R,3R)-8-[(1aR,7S,7aS)-4,6-dihydroxy-1a-(4-hydroxyphenyl)-7,7a-dihydrooxireno[2,3-b]chromen-7-yl]-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Synonyms:
Standard InCHIKey:	XYEGSUHAUOGTBV-OUECKCITSA-N
Standard InCHI:	InChI=1S/C30H24O11/c31-14-4-2-13(3-5-14)30-29(41-30)26(24-20(36)8-15(32)9-23(24)40-30)25-21(37)11-18(34)16-10-22(38)27(39-28(16)25)12-1-6-17(33)19(35)7-12/h1-9,11,22,26-27,29,31-38H,10H2/t22-,26+,27-,29+,30+/m1/s1
SMILES:	c1cc(c(cc1[C@@H]1[C@@H](Cc2c(cc(c([C@@H]3c4c(cc(cc4O[C@]4(c5ccc(cc5)O)[C@H]3O4)O)O)c2O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3120539
PubChem CID:	76317952
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	flowers	n.a.	n.a.	PMID[12193020]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24485782]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28679	Prunus mume	Species	Rosaceae	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
Others	10

Activity Type	# Activity
Individual Protein	4
NON-MOLECULAR	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4416	Individual Protein	Tartrate-resistant acid phosphatase type 5	Mus musculus	Inhibition	=	85.61	%	PMID[496367]
NPT4416	Individual Protein	Tartrate-resistant acid phosphatase type 5	Mus musculus	Inhibition	=	173.98	%	PMID[496367]
NPT4416	Individual Protein	Tartrate-resistant acid phosphatase type 5	Mus musculus	Inhibition	=	78.48	%	PMID[496367]
NPT4416	Individual Protein	Tartrate-resistant acid phosphatase type 5	Mus musculus	Inhibition	=	159.49	%	PMID[496367]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	89.84	%	PMID[496367]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	151.36	%	PMID[496367]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	77.16	%	PMID[496367]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	179.68	%	PMID[496367]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	29.9	uM	PMID[496367]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	5.42	uM	PMID[496367]

☑ 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 NPC306267 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	552
0.1-0.2	1939
0.2-0.3	5053
0.3-0.4	11083
0.4-0.5	6860
0.5-0.6	4799
0.6-0.7	7032
0.7-0.8	4449
0.8-0.85	724
0.85-0.9	144
0.9-0.95	53
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC20050
0.9795	High Similarity	NPC469944
0.9795	High Similarity	NPC44192
0.9795	High Similarity	NPC272552
0.9795	High Similarity	NPC226108
0.9795	High Similarity	NPC46283
0.9795	High Similarity	NPC322899
0.9795	High Similarity	NPC134911
0.9586	High Similarity	NPC18185
0.9586	High Similarity	NPC262911
0.9586	High Similarity	NPC294558
0.9586	High Similarity	NPC170103
0.9586	High Similarity	NPC70409
0.9586	High Similarity	NPC204770
0.9586	High Similarity	NPC58190
0.9586	High Similarity	NPC236202
0.9586	High Similarity	NPC108811
0.9586	High Similarity	NPC202742
0.9586	High Similarity	NPC263940
0.9586	High Similarity	NPC82917
0.9517	High Similarity	NPC96576
0.947	High Similarity	NPC73517
0.947	High Similarity	NPC4809
0.947	High Similarity	NPC147743
0.9456	High Similarity	NPC211561
0.9408	High Similarity	NPC205613
0.9408	High Similarity	NPC185231
0.9408	High Similarity	NPC159526
0.9408	High Similarity	NPC86630
0.9408	High Similarity	NPC106601
0.9408	High Similarity	NPC471404
0.9408	High Similarity	NPC212614
0.9408	High Similarity	NPC151474
0.9388	High Similarity	NPC20757
0.9388	High Similarity	NPC227516
0.9384	High Similarity	NPC248053
0.9384	High Similarity	NPC155564
0.9384	High Similarity	NPC102280
0.9267	High Similarity	NPC279406
0.9267	High Similarity	NPC226809
0.9262	High Similarity	NPC477612
0.9247	High Similarity	NPC171932
0.9247	High Similarity	NPC28440
0.9226	High Similarity	NPC12326
0.9205	High Similarity	NPC224161
0.9172	High Similarity	NPC277331
0.9172	High Similarity	NPC100482
0.9172	High Similarity	NPC178054
0.9145	High Similarity	NPC46335
0.9139	High Similarity	NPC59692
0.9116	High Similarity	NPC138227
0.9116	High Similarity	NPC168579
0.9116	High Similarity	NPC76176
0.9116	High Similarity	NPC469313
0.9097	High Similarity	NPC1253
0.9097	High Similarity	NPC100936
0.9073	High Similarity	NPC471403
0.9073	High Similarity	NPC259707
0.906	High Similarity	NPC15538
0.906	High Similarity	NPC473480
0.9048	High Similarity	NPC37793
0.9	High Similarity	NPC280945
0.8993	High Similarity	NPC125755
0.8973	High Similarity	NPC262189
0.8926	High Similarity	NPC277867
0.8926	High Similarity	NPC161700
0.8926	High Similarity	NPC23807
0.8889	High Similarity	NPC21902
0.8889	High Similarity	NPC233467
0.8882	High Similarity	NPC472709
0.8882	High Similarity	NPC472710
0.8874	High Similarity	NPC281549
0.8867	High Similarity	NPC260397
0.8867	High Similarity	NPC190714
0.8867	High Similarity	NPC99515
0.8859	High Similarity	NPC304894
0.8859	High Similarity	NPC473108
0.8859	High Similarity	NPC475492
0.8859	High Similarity	NPC151704
0.8859	High Similarity	NPC15659
0.8844	High Similarity	NPC22317
0.8836	High Similarity	NPC474390
0.8831	High Similarity	NPC78809
0.8824	High Similarity	NPC473621
0.8816	High Similarity	NPC318373
0.8816	High Similarity	NPC321657
0.88	High Similarity	NPC271076
0.88	High Similarity	NPC475096
0.8792	High Similarity	NPC173203
0.8792	High Similarity	NPC473044
0.8792	High Similarity	NPC163508
0.879	High Similarity	NPC24339
0.879	High Similarity	NPC166456
0.879	High Similarity	NPC94220
0.879	High Similarity	NPC7543
0.879	High Similarity	NPC98083
0.8784	High Similarity	NPC469661
0.8776	High Similarity	NPC70682
0.8776	High Similarity	NPC260741
0.8774	High Similarity	NPC157333
0.8774	High Similarity	NPC8712
0.8767	High Similarity	NPC470802
0.8758	High Similarity	NPC218041
0.8758	High Similarity	NPC469707
0.8758	High Similarity	NPC182368
0.8758	High Similarity	NPC185955
0.8758	High Similarity	NPC9933
0.8758	High Similarity	NPC225815
0.8758	High Similarity	NPC214326
0.8758	High Similarity	NPC145979
0.8758	High Similarity	NPC469706
0.8758	High Similarity	NPC260781
0.875	High Similarity	NPC270751
0.875	High Similarity	NPC329836
0.875	High Similarity	NPC175976
0.8733	High Similarity	NPC473045
0.8733	High Similarity	NPC25292
0.8733	High Similarity	NPC472155
0.8725	High Similarity	NPC204347
0.8725	High Similarity	NPC189115
0.8725	High Similarity	NPC59841
0.8725	High Similarity	NPC475891
0.8725	High Similarity	NPC475084
0.8725	High Similarity	NPC2613
0.8716	High Similarity	NPC291101
0.8716	High Similarity	NPC61783
0.8716	High Similarity	NPC266197
0.8716	High Similarity	NPC20520
0.8707	High Similarity	NPC211549
0.8701	High Similarity	NPC321972
0.8701	High Similarity	NPC324517
0.8701	High Similarity	NPC329343
0.8699	High Similarity	NPC473413
0.8699	High Similarity	NPC164787
0.8696	High Similarity	NPC9309
0.8693	High Similarity	NPC476969
0.8684	High Similarity	NPC15956
0.8684	High Similarity	NPC224674
0.8684	High Similarity	NPC99183
0.8684	High Similarity	NPC275284
0.8684	High Similarity	NPC114505
0.8684	High Similarity	NPC193473
0.8684	High Similarity	NPC101376
0.8684	High Similarity	NPC227902
0.8684	High Similarity	NPC213074
0.8684	High Similarity	NPC474397
0.8684	High Similarity	NPC39657
0.8684	High Similarity	NPC31325
0.8679	High Similarity	NPC124747
0.8679	High Similarity	NPC155754
0.8679	High Similarity	NPC109061
0.8675	High Similarity	NPC472154
0.8675	High Similarity	NPC181615
0.8667	High Similarity	NPC252169
0.8667	High Similarity	NPC472451
0.8667	High Similarity	NPC81638
0.8662	High Similarity	NPC165483
0.8658	High Similarity	NPC35216
0.8658	High Similarity	NPC263261
0.8658	High Similarity	NPC471389
0.8658	High Similarity	NPC87725
0.8654	High Similarity	NPC159922
0.8649	High Similarity	NPC22517
0.8649	High Similarity	NPC32630
0.8645	High Similarity	NPC476391
0.8645	High Similarity	NPC325860
0.8639	High Similarity	NPC242028
0.8639	High Similarity	NPC265433
0.8639	High Similarity	NPC270456
0.8639	High Similarity	NPC269091
0.8639	High Similarity	NPC162659
0.8639	High Similarity	NPC203230
0.8639	High Similarity	NPC248727
0.8639	High Similarity	NPC302701
0.8639	High Similarity	NPC16435
0.8639	High Similarity	NPC306441
0.8636	High Similarity	NPC238140
0.863	High Similarity	NPC66840
0.863	High Similarity	NPC256307
0.8627	High Similarity	NPC473876
0.8621	High Similarity	NPC15658
0.8621	High Similarity	NPC61477
0.8621	High Similarity	NPC126029
0.8621	High Similarity	NPC185604
0.8621	High Similarity	NPC219876
0.8621	High Similarity	NPC261619
0.8621	High Similarity	NPC78770
0.8618	High Similarity	NPC268515
0.8618	High Similarity	NPC324492
0.8618	High Similarity	NPC95652
0.8618	High Similarity	NPC274454
0.8618	High Similarity	NPC150714
0.8618	High Similarity	NPC40222
0.8618	High Similarity	NPC215678
0.8618	High Similarity	NPC317053
0.8609	High Similarity	NPC225445
0.8609	High Similarity	NPC45257
0.8609	High Similarity	NPC280092
0.8609	High Similarity	NPC93323
0.8609	High Similarity	NPC12641

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 NPC306267 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	446
0.1-0.2	948
0.2-0.3	2107
0.3-0.4	2733
0.4-0.5	1512
0.5-0.6	872
0.6-0.7	457
0.7-0.8	70
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8621	High Similarity	NPD1612	Clinical (unspecified phase)
0.8621	High Similarity	NPD1613	Approved
0.8356	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD4908	Phase 1
0.8163	Intermediate Similarity	NPD3027	Phase 3
0.8084	Intermediate Similarity	NPD7228	Approved
0.8075	Intermediate Similarity	NPD8455	Phase 2
0.8052	Intermediate Similarity	NPD6674	Discontinued
0.7988	Intermediate Similarity	NPD7074	Phase 3
0.7987	Intermediate Similarity	NPD1653	Approved
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6166	Phase 2
0.7964	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7054	Approved
0.7882	Intermediate Similarity	NPD7472	Approved
0.7879	Intermediate Similarity	NPD6234	Discontinued
0.7862	Intermediate Similarity	NPD1610	Phase 2
0.7836	Intermediate Similarity	NPD6797	Phase 2
0.7791	Intermediate Similarity	NPD7251	Discontinued
0.7791	Intermediate Similarity	NPD37	Approved
0.7784	Intermediate Similarity	NPD7199	Phase 2
0.7758	Intermediate Similarity	NPD4965	Approved
0.7758	Intermediate Similarity	NPD4967	Phase 2
0.7758	Intermediate Similarity	NPD4966	Approved
0.7744	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD3787	Discontinued
0.7692	Intermediate Similarity	NPD7266	Discontinued
0.7667	Intermediate Similarity	NPD2861	Phase 2
0.7661	Intermediate Similarity	NPD3818	Discontinued
0.7644	Intermediate Similarity	NPD7808	Phase 3
0.7619	Intermediate Similarity	NPD1091	Approved
0.7616	Intermediate Similarity	NPD5844	Phase 1
0.7616	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8312	Approved
0.76	Intermediate Similarity	NPD8313	Approved
0.7588	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7240	Approved
0.7576	Intermediate Similarity	NPD1934	Approved
0.7574	Intermediate Similarity	NPD6959	Discontinued
0.7566	Intermediate Similarity	NPD4625	Phase 3
0.7543	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6559	Discontinued
0.7484	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1548	Phase 1
0.7457	Intermediate Similarity	NPD3751	Discontinued
0.7455	Intermediate Similarity	NPD4380	Phase 2
0.7419	Intermediate Similarity	NPD4060	Phase 1
0.74	Intermediate Similarity	NPD4749	Approved
0.7389	Intermediate Similarity	NPD7097	Phase 1
0.7381	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5124	Phase 1
0.7372	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8053	Approved
0.736	Intermediate Similarity	NPD8054	Approved
0.7346	Intermediate Similarity	NPD5058	Phase 3
0.7321	Intermediate Similarity	NPD1465	Phase 2
0.731	Intermediate Similarity	NPD5494	Approved
0.7301	Intermediate Similarity	NPD7213	Phase 3
0.7301	Intermediate Similarity	NPD7212	Phase 2
0.7293	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7680	Approved
0.7258	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7447	Phase 1
0.7256	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7549	Discontinued
0.7241	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7768	Phase 2
0.7233	Intermediate Similarity	NPD5960	Phase 3
0.7225	Intermediate Similarity	NPD6232	Discontinued
0.7222	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2801	Approved
0.7208	Intermediate Similarity	NPD3018	Phase 2
0.72	Intermediate Similarity	NPD7473	Discontinued
0.7197	Intermediate Similarity	NPD3620	Phase 2
0.7197	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD1511	Approved
0.7193	Intermediate Similarity	NPD7075	Discontinued
0.7193	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4536	Approved
0.717	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4538	Approved
0.7125	Intermediate Similarity	NPD5588	Approved
0.7124	Intermediate Similarity	NPD8651	Approved
0.7108	Intermediate Similarity	NPD1512	Approved
0.7101	Intermediate Similarity	NPD7411	Suspended
0.7101	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7685	Pre-registration
0.7076	Intermediate Similarity	NPD3817	Phase 2
0.7059	Intermediate Similarity	NPD2982	Phase 2
0.7059	Intermediate Similarity	NPD2983	Phase 2
0.7055	Intermediate Similarity	NPD1652	Phase 2
0.7039	Intermediate Similarity	NPD3705	Approved
0.7037	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3882	Suspended
0.7032	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8156	Discontinued
0.7018	Intermediate Similarity	NPD7819	Suspended
0.7018	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD4577	Approved
0.7017	Intermediate Similarity	NPD4578	Approved
0.7007	Intermediate Similarity	NPD5283	Phase 1
0.6995	Remote Similarity	NPD4663	Approved
0.6993	Remote Similarity	NPD2981	Phase 2
0.6988	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5402	Approved
0.6971	Remote Similarity	NPD8127	Discontinued
0.697	Remote Similarity	NPD6190	Approved
0.6966	Remote Similarity	NPD8099	Discontinued
0.6966	Remote Similarity	NPD8252	Approved
0.6966	Remote Similarity	NPD8251	Approved
0.6964	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6798	Discontinued
0.6962	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6801	Discontinued
0.6948	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5735	Approved
0.6933	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5763	Approved
0.6933	Remote Similarity	NPD5762	Approved
0.6932	Remote Similarity	NPD7229	Phase 3
0.6923	Remote Similarity	NPD7313	Approved
0.6923	Remote Similarity	NPD7311	Approved
0.6923	Remote Similarity	NPD7312	Approved
0.6923	Remote Similarity	NPD7310	Approved
0.6923	Remote Similarity	NPD8151	Discontinued
0.6914	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7157	Approved
0.6909	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3750	Approved
0.6909	Remote Similarity	NPD7466	Approved
0.6909	Remote Similarity	NPD3892	Phase 2
0.6908	Remote Similarity	NPD6516	Phase 2
0.6908	Remote Similarity	NPD5126	Approved
0.6908	Remote Similarity	NPD5846	Approved
0.6908	Remote Similarity	NPD5125	Phase 3
0.689	Remote Similarity	NPD1549	Phase 2
0.6886	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7041	Phase 2
0.6885	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7309	Approved
0.6871	Remote Similarity	NPD6100	Approved
0.6871	Remote Similarity	NPD6099	Approved
0.6871	Remote Similarity	NPD228	Approved
0.6865	Remote Similarity	NPD7906	Approved
0.6864	Remote Similarity	NPD5403	Approved
0.6854	Remote Similarity	NPD27	Approved
0.6854	Remote Similarity	NPD2489	Approved
0.6849	Remote Similarity	NPD3021	Approved
0.6849	Remote Similarity	NPD3022	Approved
0.6848	Remote Similarity	NPD5177	Phase 3
0.6845	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1357	Approved
0.6836	Remote Similarity	NPD3051	Approved
0.6832	Remote Similarity	NPD6355	Discontinued
0.6824	Remote Similarity	NPD7843	Approved
0.6818	Remote Similarity	NPD422	Phase 1
0.6815	Remote Similarity	NPD6584	Phase 3
0.6813	Remote Similarity	NPD6233	Phase 2
0.681	Remote Similarity	NPD4108	Discontinued
0.6807	Remote Similarity	NPD6331	Phase 2
0.68	Remote Similarity	NPD6671	Approved
0.6798	Remote Similarity	NPD2969	Approved
0.6798	Remote Similarity	NPD2970	Approved
0.6792	Remote Similarity	NPD7095	Approved
0.6788	Remote Similarity	NPD7037	Approved
0.6788	Remote Similarity	NPD2424	Discontinued
0.6784	Remote Similarity	NPD7458	Discontinued
0.6782	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD2684	Approved
0.6774	Remote Similarity	NPD6842	Approved
0.6774	Remote Similarity	NPD6841	Approved
0.6774	Remote Similarity	NPD6843	Phase 3
0.6771	Remote Similarity	NPD6782	Approved
0.6771	Remote Similarity	NPD6776	Approved
0.6771	Remote Similarity	NPD6777	Approved
0.6771	Remote Similarity	NPD6779	Approved
0.6771	Remote Similarity	NPD6778	Approved
0.6771	Remote Similarity	NPD6780	Approved
0.6771	Remote Similarity	NPD6781	Approved
0.677	Remote Similarity	NPD1558	Phase 1
0.677	Remote Similarity	NPD4140	Approved
0.6768	Remote Similarity	NPD7783	Phase 2
0.6768	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2677	Approved
0.6766	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7119	Phase 2
0.6747	Remote Similarity	NPD7421	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