NPASS Compound

Structure

CID254351 OpenBabel06191716052D 40 45 0 0 0 0 0 0 0 0999 V2000 -1.6944 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7776 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9304 -2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7776 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9304 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9304 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2360 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9304 -3.4239 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6248 -0.4891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -2.9348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7776 0.9783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 -0.4891 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 3 1 0 0 0 0 1 13 2 0 0 0 0 2 4 2 0 0 0 0 2 13 1 0 0 0 0 3 14 2 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 15 1 0 0 0 0 6 17 1 0 0 0 0 7 15 2 0 0 0 0 7 18 1 0 0 0 0 8 16 2 0 0 0 0 8 19 1 0 0 0 0 9 16 1 0 0 0 0 9 26 2 0 0 0 0 10 20 2 0 0 0 0 10 21 1 0 0 0 0 11 23 1 0 0 0 0 11 24 2 0 0 0 0 12 22 1 0 0 0 0 12 25 2 0 0 0 0 13 24 1 0 0 0 0 14 31 1 0 0 0 0 15 32 1 0 0 0 0 16 33 1 0 0 0 0 17 18 2 0 0 0 0 17 25 1 0 0 0 0 18 27 1 0 0 0 0 19 28 2 0 0 0 0 19 34 1 0 0 0 0 20 27 1 0 0 0 0 20 35 1 0 0 0 0 21 29 2 0 0 0 0 21 36 1 0 0 0 0 22 28 1 0 0 0 0 22 37 2 0 0 0 0 23 29 1 0 0 0 0 23 38 2 0 0 0 0 24 40 1 0 0 0 0 25 39 1 0 0 0 0 26 28 1 0 0 0 0 26 39 1 0 0 0 0 27 30 2 0 0 0 0 29 30 1 0 0 0 0 30 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.09
Volume:	521.816
LogP:	5.661
LogD:	2.457
LogS:	-5.267
# Rotatable Bonds:	3
TPSA:	181.8
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.177
Synthetic Accessibility Score:	3.089
Fsp3:	0.0
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:	-5.235
MDCK Permeability:	8.193659596145153e-06
Pgp-inhibitor:	0.014
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.596
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	95.80115509033203%
Volume Distribution (VD):	0.504
Pgp-substrate:	5.634698867797852%

ADMET: Metabolism

CYP1A2-inhibitor:	0.927
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.644
CYP2C19-substrate:	0.033
CYP2C9-inhibitor:	0.565
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.189
CYP2D6-substrate:	0.538
CYP3A4-inhibitor:	0.275
CYP3A4-substrate:	0.052

ADMET: Excretion

Clearance (CL):	4.304
Half-life (T1/2):	0.728

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.172
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.813
Skin Sensitization:	0.877
Carcinogencity:	0.035
Eye Corrosion:	0.003
Eye Irritation:	0.901
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC254351

Natural Product ID:	NPC254351
*Common Name:**	2',8''-Biapigenin
IUPAC Name:	8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:	2',8'-Biapigenin
Standard InCHIKey:	IDXPHFRRYHNPFG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H18O10/c31-14-3-1-13(2-4-14)24-11-23(38)29-21(36)10-20(35)27(30(29)40-24)18-7-15(32)5-6-17(18)25-12-22(37)28-19(34)8-16(33)9-26(28)39-25/h1-12,31-36H
SMILES:	Oc1ccc(c(c1)c1c(O)cc(c2c1oc(cc2=O)c1ccc(cc1)O)O)c1cc(=O)c2c(o1)cc(cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL271347
PubChem CID:	11958336
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones

*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
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20335035]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25559759]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29144743]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31244143]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	50.0	%	PMID[501438]

☑ 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 NPC254351 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	627
0.1-0.2	2278
0.2-0.3	5217
0.3-0.4	11908
0.4-0.5	5388
0.5-0.6	4621
0.6-0.7	5378
0.7-0.8	4816
0.8-0.85	1949
0.85-0.9	454
0.9-0.95	57
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC18699
0.98	High Similarity	NPC55443
0.9669	High Similarity	NPC177650
0.9662	High Similarity	NPC67322
0.9662	High Similarity	NPC111112
0.9662	High Similarity	NPC222713
0.9662	High Similarity	NPC138299
0.9605	High Similarity	NPC186325
0.9605	High Similarity	NPC312993
0.9542	High Similarity	NPC189552
0.9542	High Similarity	NPC273467
0.9533	High Similarity	NPC290830
0.9533	High Similarity	NPC71061
0.9533	High Similarity	NPC303485
0.9533	High Similarity	NPC72425
0.9533	High Similarity	NPC194593
0.9527	High Similarity	NPC288840
0.9527	High Similarity	NPC291746
0.947	High Similarity	NPC158027
0.947	High Similarity	NPC186227
0.947	High Similarity	NPC14606
0.947	High Similarity	NPC52611
0.947	High Similarity	NPC159707
0.947	High Similarity	NPC248739
0.947	High Similarity	NPC205026
0.947	High Similarity	NPC215203
0.947	High Similarity	NPC265624
0.947	High Similarity	NPC150908
0.947	High Similarity	NPC121649
0.947	High Similarity	NPC100049
0.9359	High Similarity	NPC469664
0.9342	High Similarity	NPC182555
0.9342	High Similarity	NPC66441
0.9286	High Similarity	NPC195167
0.9276	High Similarity	NPC329844
0.9236	High Similarity	NPC259757
0.9226	High Similarity	NPC292863
0.9226	High Similarity	NPC184326
0.9216	High Similarity	NPC134171
0.9216	High Similarity	NPC300668
0.9211	High Similarity	NPC174086
0.9184	High Similarity	NPC14871
0.9167	High Similarity	NPC137232
0.9167	High Similarity	NPC18380
0.9156	High Similarity	NPC32867
0.9156	High Similarity	NPC56049
0.9156	High Similarity	NPC54830
0.9139	High Similarity	NPC10027
0.9139	High Similarity	NPC97029
0.9139	High Similarity	NPC65589
0.9139	High Similarity	NPC288036
0.9139	High Similarity	NPC158338
0.9139	High Similarity	NPC100985
0.9139	High Similarity	NPC97028
0.9139	High Similarity	NPC65775
0.9108	High Similarity	NPC15374
0.9103	High Similarity	NPC121647
0.9091	High Similarity	NPC66508
0.9091	High Similarity	NPC166054
0.9091	High Similarity	NPC226656
0.9091	High Similarity	NPC55662
0.9073	High Similarity	NPC106328
0.9073	High Similarity	NPC122894
0.9073	High Similarity	NPC7025
0.9073	High Similarity	NPC27221
0.9073	High Similarity	NPC35150
0.9073	High Similarity	NPC256672
0.9051	High Similarity	NPC290160
0.9045	High Similarity	NPC301256
0.9045	High Similarity	NPC312273
0.9038	High Similarity	NPC51760
0.9038	High Similarity	NPC295090
0.9032	High Similarity	NPC69531
0.9026	High Similarity	NPC95842
0.9026	High Similarity	NPC178964
0.9026	High Similarity	NPC324447
0.9026	High Similarity	NPC121568
0.9026	High Similarity	NPC280530
0.9026	High Similarity	NPC169990
0.9026	High Similarity	NPC210942
0.902	High Similarity	NPC149526
0.902	High Similarity	NPC258249
0.902	High Similarity	NPC474417
0.9013	High Similarity	NPC3642
0.9013	High Similarity	NPC473978
0.9007	High Similarity	NPC123202
0.9007	High Similarity	NPC7943
0.9007	High Similarity	NPC22005
0.9	High Similarity	NPC278175
0.9	High Similarity	NPC257236
0.8993	High Similarity	NPC59739
0.8993	High Similarity	NPC299080
0.8993	High Similarity	NPC78803
0.8993	High Similarity	NPC293852
0.8993	High Similarity	NPC217083
0.8993	High Similarity	NPC214236
0.8993	High Similarity	NPC62840
0.8987	High Similarity	NPC473012
0.8987	High Similarity	NPC473011
0.8981	High Similarity	NPC472052
0.8981	High Similarity	NPC472060
0.8981	High Similarity	NPC470342
0.8974	High Similarity	NPC268360
0.8974	High Similarity	NPC1796
0.8974	High Similarity	NPC475184
0.8974	High Similarity	NPC257166
0.8974	High Similarity	NPC183
0.8974	High Similarity	NPC112954
0.8961	High Similarity	NPC115601
0.8961	High Similarity	NPC39154
0.8961	High Similarity	NPC78324
0.8961	High Similarity	NPC208011
0.8954	High Similarity	NPC227122
0.8938	High Similarity	NPC30027
0.8938	High Similarity	NPC171985
0.8938	High Similarity	NPC320741
0.8933	High Similarity	NPC219915
0.8933	High Similarity	NPC11700
0.8931	High Similarity	NPC473009
0.8926	High Similarity	NPC26238
0.8919	High Similarity	NPC216978
0.8919	High Similarity	NPC303633
0.8919	High Similarity	NPC55018
0.8919	High Similarity	NPC220062
0.8919	High Similarity	NPC301217
0.8919	High Similarity	NPC96565
0.8917	High Similarity	NPC105584
0.8917	High Similarity	NPC15815
0.8917	High Similarity	NPC324736
0.8917	High Similarity	NPC51247
0.891	High Similarity	NPC192587
0.891	High Similarity	NPC137100
0.8903	High Similarity	NPC214632
0.8903	High Similarity	NPC235333
0.8902	High Similarity	NPC216307
0.8896	High Similarity	NPC478148
0.8896	High Similarity	NPC72958
0.8896	High Similarity	NPC305965
0.8896	High Similarity	NPC232645
0.8889	High Similarity	NPC329933
0.8882	High Similarity	NPC237635
0.8882	High Similarity	NPC79469
0.8882	High Similarity	NPC34802
0.8882	High Similarity	NPC475348
0.8882	High Similarity	NPC286230
0.8882	High Similarity	NPC166757
0.8882	High Similarity	NPC14001
0.8882	High Similarity	NPC12305
0.8882	High Similarity	NPC24673
0.8882	High Similarity	NPC201731
0.8882	High Similarity	NPC104406
0.8882	High Similarity	NPC97716
0.8882	High Similarity	NPC261271
0.8882	High Similarity	NPC253730
0.8875	High Similarity	NPC169471
0.8875	High Similarity	NPC473010
0.8874	High Similarity	NPC319752
0.8874	High Similarity	NPC470135
0.8874	High Similarity	NPC194949
0.8874	High Similarity	NPC39045
0.8874	High Similarity	NPC470136
0.8874	High Similarity	NPC282957
0.8868	High Similarity	NPC3448
0.8868	High Similarity	NPC477239
0.8867	High Similarity	NPC310340
0.8861	High Similarity	NPC42965
0.8861	High Similarity	NPC195136
0.8861	High Similarity	NPC226462
0.8861	High Similarity	NPC98023
0.8859	High Similarity	NPC241100
0.8859	High Similarity	NPC159275
0.8859	High Similarity	NPC172986
0.8859	High Similarity	NPC261227
0.8859	High Similarity	NPC275734
0.8859	High Similarity	NPC270883
0.8854	High Similarity	NPC318527
0.8854	High Similarity	NPC324358
0.8854	High Similarity	NPC322459
0.8854	High Similarity	NPC323627
0.8851	High Similarity	NPC201395
0.8846	High Similarity	NPC297531
0.8846	High Similarity	NPC213936
0.8846	High Similarity	NPC201227
0.8846	High Similarity	NPC37253
0.8846	High Similarity	NPC99199
0.8846	High Similarity	NPC79375
0.8846	High Similarity	NPC148938
0.8846	High Similarity	NPC258474
0.8839	High Similarity	NPC40356
0.8839	High Similarity	NPC154683
0.8839	High Similarity	NPC87708
0.8839	High Similarity	NPC45934
0.8831	High Similarity	NPC309979
0.8831	High Similarity	NPC307780
0.8831	High Similarity	NPC151973
0.8831	High Similarity	NPC472633
0.8827	High Similarity	NPC300307
0.8827	High Similarity	NPC107627
0.8824	High Similarity	NPC152233
0.8824	High Similarity	NPC161191

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 NPC254351 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	547
0.1-0.2	1046
0.2-0.3	1739
0.3-0.4	2776
0.4-0.5	1733
0.5-0.6	909
0.6-0.7	245
0.7-0.8	119
0.8-0.85	24
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD6959	Discontinued
0.9	High Similarity	NPD7410	Clinical (unspecified phase)
0.8758	High Similarity	NPD7852	Clinical (unspecified phase)
0.875	High Similarity	NPD4378	Clinical (unspecified phase)
0.8726	High Similarity	NPD8443	Clinical (unspecified phase)
0.8684	High Similarity	NPD7390	Discontinued
0.8662	High Similarity	NPD7819	Suspended
0.8616	High Similarity	NPD3749	Approved
0.8553	High Similarity	NPD7768	Phase 2
0.8535	High Similarity	NPD7411	Suspended
0.8487	Intermediate Similarity	NPD3750	Approved
0.8471	Intermediate Similarity	NPD4380	Phase 2
0.8442	Intermediate Similarity	NPD1511	Approved
0.8428	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD6232	Discontinued
0.84	Intermediate Similarity	NPD1510	Phase 2
0.8364	Intermediate Similarity	NPD7473	Discontinued
0.8355	Intermediate Similarity	NPD1549	Phase 2
0.8333	Intermediate Similarity	NPD1512	Approved
0.8303	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6166	Phase 2
0.8235	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD2796	Approved
0.8199	Intermediate Similarity	NPD2801	Approved
0.816	Intermediate Similarity	NPD7075	Discontinued
0.816	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD3748	Approved
0.8137	Intermediate Similarity	NPD1934	Approved
0.8133	Intermediate Similarity	NPD1240	Approved
0.8105	Intermediate Similarity	NPD5404	Approved
0.8105	Intermediate Similarity	NPD5408	Approved
0.8105	Intermediate Similarity	NPD5406	Approved
0.8105	Intermediate Similarity	NPD5405	Approved
0.8063	Intermediate Similarity	NPD3226	Approved
0.8047	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD5844	Phase 1
0.8039	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1607	Approved
0.8025	Intermediate Similarity	NPD6801	Discontinued
0.7988	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD2800	Approved
0.7949	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7054	Approved
0.7927	Intermediate Similarity	NPD3817	Phase 2
0.7925	Intermediate Similarity	NPD2533	Approved
0.7925	Intermediate Similarity	NPD2532	Approved
0.7925	Intermediate Similarity	NPD2534	Approved
0.7895	Intermediate Similarity	NPD7472	Approved
0.7895	Intermediate Similarity	NPD7074	Phase 3
0.7882	Intermediate Similarity	NPD3818	Discontinued
0.7879	Intermediate Similarity	NPD3882	Suspended
0.7866	Intermediate Similarity	NPD1465	Phase 2
0.7849	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6797	Phase 2
0.7844	Intermediate Similarity	NPD5494	Approved
0.7834	Intermediate Similarity	NPD1243	Approved
0.7826	Intermediate Similarity	NPD5403	Approved
0.7821	Intermediate Similarity	NPD2344	Approved
0.7818	Intermediate Similarity	NPD5402	Approved
0.7816	Intermediate Similarity	NPD8312	Approved
0.7816	Intermediate Similarity	NPD8313	Approved
0.7803	Intermediate Similarity	NPD7251	Discontinued
0.7803	Intermediate Similarity	NPD6559	Discontinued
0.7763	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7808	Phase 3
0.7756	Intermediate Similarity	NPD2935	Discontinued
0.7756	Intermediate Similarity	NPD6100	Approved
0.7756	Intermediate Similarity	NPD6099	Approved
0.775	Intermediate Similarity	NPD6799	Approved
0.773	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2346	Discontinued
0.7702	Intermediate Similarity	NPD5401	Approved
0.7697	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4625	Phase 3
0.7692	Intermediate Similarity	NPD2799	Discontinued
0.7688	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6599	Discontinued
0.7677	Intermediate Similarity	NPD6651	Approved
0.7673	Intermediate Similarity	NPD7003	Approved
0.7657	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2313	Discontinued
0.7643	Intermediate Similarity	NPD1551	Phase 2
0.7635	Intermediate Similarity	NPD1201	Approved
0.7632	Intermediate Similarity	NPD4908	Phase 1
0.7625	Intermediate Similarity	NPD2309	Approved
0.7611	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD920	Approved
0.7602	Intermediate Similarity	NPD3926	Phase 2
0.7598	Intermediate Similarity	NPD4287	Approved
0.7593	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7177	Discontinued
0.755	Intermediate Similarity	NPD1470	Approved
0.7548	Intermediate Similarity	NPD943	Approved
0.7544	Intermediate Similarity	NPD3787	Discontinued
0.7544	Intermediate Similarity	NPD7229	Phase 3
0.7543	Intermediate Similarity	NPD5953	Discontinued
0.7532	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4288	Approved
0.7485	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7471	Intermediate Similarity	NPD919	Approved
0.7453	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD8455	Phase 2
0.7434	Intermediate Similarity	NPD1203	Approved
0.7419	Intermediate Similarity	NPD3268	Approved
0.7419	Intermediate Similarity	NPD3764	Approved
0.7394	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2798	Approved
0.7384	Intermediate Similarity	NPD7199	Phase 2
0.7384	Intermediate Similarity	NPD1247	Approved
0.7382	Intermediate Similarity	NPD8151	Discontinued
0.7368	Intermediate Similarity	NPD3225	Approved
0.7351	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD5710	Approved
0.7341	Intermediate Similarity	NPD5711	Approved
0.7337	Intermediate Similarity	NPD4363	Phase 3
0.7337	Intermediate Similarity	NPD4360	Phase 2
0.733	Intermediate Similarity	NPD7286	Phase 2
0.7326	Intermediate Similarity	NPD6777	Approved
0.7326	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6780	Approved
0.7326	Intermediate Similarity	NPD6781	Approved
0.7326	Intermediate Similarity	NPD6778	Approved
0.7326	Intermediate Similarity	NPD6776	Approved
0.7326	Intermediate Similarity	NPD6782	Approved
0.7326	Intermediate Similarity	NPD6779	Approved
0.732	Intermediate Similarity	NPD2797	Approved
0.7305	Intermediate Similarity	NPD7458	Discontinued
0.7299	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1610	Phase 2
0.7263	Intermediate Similarity	NPD7870	Phase 2
0.7263	Intermediate Similarity	NPD7871	Phase 2
0.725	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1548	Phase 1
0.7239	Intermediate Similarity	NPD4628	Phase 3
0.7237	Intermediate Similarity	NPD1608	Approved
0.7229	Intermediate Similarity	NPD6273	Approved
0.7216	Intermediate Similarity	NPD7783	Phase 2
0.7216	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7698	Approved
0.7211	Intermediate Similarity	NPD7696	Phase 3
0.7211	Intermediate Similarity	NPD7435	Discontinued
0.7211	Intermediate Similarity	NPD7697	Approved
0.7204	Intermediate Similarity	NPD4361	Phase 2
0.7204	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6832	Phase 2
0.7171	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD422	Phase 1
0.717	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5124	Phase 1
0.716	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7124	Intermediate Similarity	NPD9717	Approved
0.7115	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD8150	Discontinued
0.7097	Intermediate Similarity	NPD3266	Approved
0.7097	Intermediate Similarity	NPD1164	Approved
0.7097	Intermediate Similarity	NPD3267	Approved
0.7093	Intermediate Similarity	NPD2296	Approved
0.7086	Intermediate Similarity	NPD1651	Approved
0.7078	Intermediate Similarity	NPD4749	Approved
0.7076	Intermediate Similarity	NPD37	Approved
0.7069	Intermediate Similarity	NPD6234	Discontinued
0.7068	Intermediate Similarity	NPD6823	Phase 2
0.7062	Intermediate Similarity	NPD7701	Phase 2
0.7059	Intermediate Similarity	NPD6535	Approved
0.7059	Intermediate Similarity	NPD6534	Approved
0.7052	Intermediate Similarity	NPD4965	Approved
0.7052	Intermediate Similarity	NPD4967	Phase 2
0.7052	Intermediate Similarity	NPD4966	Approved
0.7039	Intermediate Similarity	NPD17	Approved
0.7032	Intermediate Similarity	NPD1283	Approved
0.7	Intermediate Similarity	NPD4060	Phase 1
0.7	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1613	Approved
0.699	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7874	Approved
0.6983	Remote Similarity	NPD7228	Approved
0.6981	Remote Similarity	NPD1296	Phase 2
0.6981	Remote Similarity	NPD411	Approved
0.697	Remote Similarity	NPD2654	Approved
0.6964	Remote Similarity	NPD7447	Phase 1
0.6957	Remote Similarity	NPD447	Suspended
0.6957	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7801	Approved
0.6951	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7700	Phase 2
0.6947	Remote Similarity	NPD7699	Phase 2
0.6942	Remote Similarity	NPD7654	Discontinued
0.6923	Remote Similarity	NPD7584	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