NPASS Compound

Structure

NPC277331 OpenBabel07101719252D 39 44 0 0 1 0 0 0 0 0999 V2000 -4.2339 -2.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3871 -0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 2.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0807 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2339 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 2.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5403 1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 -4.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 -1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3871 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0807 -0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5403 2.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 -5.3778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 -2.4444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5403 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 1.4667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5403 -2.4444 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6936 -3.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 -3.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9778 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8468 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9275 -0.4889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3871 2.9333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 -6.3556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3871 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -3.4222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -2.9333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 2.4444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5403 -3.4222 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 5 1 0 0 0 0 1 14 2 0 0 0 0 2 6 2 0 0 0 0 2 14 1 0 0 0 0 3 7 1 0 0 0 0 3 15 2 0 0 0 0 4 8 2 0 0 0 0 4 15 1 0 0 0 0 5 16 2 0 0 0 0 6 16 1 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 9 22 1 0 0 0 0 10 18 1 0 0 0 0 10 26 2 0 0 0 0 11 19 1 0 0 0 0 11 24 1 0 0 0 0 12 20 1 0 0 0 0 12 25 1 0 0 0 0 13 21 2 0 0 0 0 13 23 1 0 0 0 0 16 31 1 0 0 0 0 17 32 1 0 0 0 0 18 33 1 0 0 0 0 19 21 1 0 0 0 0 19 30 2 0 0 0 0 20 27 1 0 0 0 0 20 28 1 1 0 0 0 21 34 1 0 0 0 0 22 27 2 0 0 0 0 22 35 1 0 0 0 0 23 28 2 0 0 0 0 23 36 1 0 0 0 0 24 29 1 0 0 0 0 24 37 1 1 0 0 0 25 14 1 6 0 0 0 25 38 1 0 0 0 0 26 27 1 0 0 0 0 26 38 1 0 0 0 0 28 30 1 0 0 0 0 29 15 1 6 0 0 0 29 39 1 0 0 0 0 30 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.16
Volume:	523.572
LogP:	4.473
LogD:	3.283
LogS:	-4.028
# Rotatable Bonds:	3
TPSA:	160.07
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.201
Synthetic Accessibility Score:	4.217
Fsp3:	0.2
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:	-6.116
MDCK Permeability:	5.649516879202565e-06
Pgp-inhibitor:	0.041
Pgp-substrate:	0.055
Human Intestinal Absorption (HIA):	0.073
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	97.54158782958984%
Volume Distribution (VD):	0.438
Pgp-substrate:	3.3496663570404053%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.349
CYP2C19-inhibitor:	0.528
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.881
CYP2C9-substrate:	0.995
CYP2D6-inhibitor:	0.291
CYP2D6-substrate:	0.538
CYP3A4-inhibitor:	0.239
CYP3A4-substrate:	0.525

ADMET: Excretion

Clearance (CL):	11.601
Half-life (T1/2):	0.79

ADMET: Toxicity

hERG Blockers:	0.137
Human Hepatotoxicity (H-HT):	0.104
Drug-inuced Liver Injury (DILI):	0.616
AMES Toxicity:	0.279
Rat Oral Acute Toxicity:	0.94
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.956
Carcinogencity:	0.101
Eye Corrosion:	0.003
Eye Irritation:	0.895
Respiratory Toxicity:	0.206

Download Data

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

Natural Product: NPC277331

Natural Product ID:	NPC277331
*Common Name:**	(2S)-4',5,7-Trihydroxyflavan-(4Beta->8)-Afzelechin
IUPAC Name:	(2R,3S)-8-[(2S,4R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Synonyms:
Standard InCHIKey:	FWNROEJRQURIKY-VGGRNRAKSA-N
Standard InCHI:	InChI=1S/C30H26O9/c31-16-5-1-14(2-6-16)25-12-20(27-22(35)9-18(33)10-26(27)38-25)28-23(36)13-21(34)19-11-24(37)29(39-30(19)28)15-3-7-17(32)8-4-15/h1-10,13,20,24-25,29,31-37H,11-12H2/t20-,24+,25+,29-/m1/s1
SMILES:	c1cc(ccc1[C@@H]1C[C@H](c2c(cc(cc2O1)O)O)c1c(cc(c2C[C@@H]([C@@H](c3ccc(cc3)O)Oc12)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2335722
PubChem CID:	71521862
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
NPO5183	Feretia apodanthera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23268742]
NPO16874	Campsiandra guayanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23268742]
NPO16874	Campsiandra guayanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5183	Feretia apodanthera	Species	Rubiaceae	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	5
Kd	2
Others	1

Activity Type	# Activity
Cell Line	2
Individual Protein	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT301	Individual Protein	Vascular endothelial growth factor receptor 1	Homo sapiens	IC50	=	15000.0	nM	PMID[524821]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	70000.0	nM	PMID[524821]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	70000.0	nM	PMID[524821]
NPT4535	Individual Protein	Vascular endothelial growth factor A	Homo sapiens	Kd	=	16.0	nM	PMID[524821]
NPT4536	Individual Protein	Placenta growth factor	Homo sapiens	Kd	=	11.0	nM	PMID[524821]
NPT301	Individual Protein	Vascular endothelial growth factor receptor 1	Homo sapiens	IC50	=	50000.0	nM	PMID[524821]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	9.79	ug	PMID[524821]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	56.19	%	PMID[524821]

☑ 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 NPC277331 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	480
0.1-0.2	1614
0.2-0.3	4374
0.3-0.4	11218
0.4-0.5	7135
0.5-0.6	4473
0.6-0.7	7349
0.7-0.8	4997
0.8-0.85	645
0.85-0.9	330
0.9-0.95	64
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC100482
0.9638	High Similarity	NPC248053
0.9638	High Similarity	NPC155564
0.9638	High Similarity	NPC102280
0.9635	High Similarity	NPC475492
0.9568	High Similarity	NPC202742
0.9568	High Similarity	NPC82917
0.9568	High Similarity	NPC70409
0.9568	High Similarity	NPC18185
0.9568	High Similarity	NPC170103
0.9568	High Similarity	NPC236202
0.9568	High Similarity	NPC58190
0.9568	High Similarity	NPC204770
0.9568	High Similarity	NPC262911
0.9568	High Similarity	NPC108811
0.9568	High Similarity	NPC294558
0.9568	High Similarity	NPC263940
0.9496	High Similarity	NPC96576
0.9433	High Similarity	NPC211561
0.9362	High Similarity	NPC20757
0.9362	High Similarity	NPC227516
0.9338	High Similarity	NPC470308
0.9338	High Similarity	NPC470307
0.9301	High Similarity	NPC259707
0.9301	High Similarity	NPC471403
0.927	High Similarity	NPC475836
0.9265	High Similarity	NPC471522
0.9259	High Similarity	NPC476615
0.9259	High Similarity	NPC476617
0.9259	High Similarity	NPC476616
0.9236	High Similarity	NPC279406
0.9236	High Similarity	NPC44192
0.9236	High Similarity	NPC469944
0.9236	High Similarity	NPC226809
0.9236	High Similarity	NPC46283
0.9236	High Similarity	NPC134911
0.9236	High Similarity	NPC322899
0.9236	High Similarity	NPC226108
0.9236	High Similarity	NPC272552
0.9231	High Similarity	NPC477612
0.9214	High Similarity	NPC28440
0.9214	High Similarity	NPC171932
0.9179	High Similarity	NPC103799
0.9172	High Similarity	NPC224161
0.9172	High Similarity	NPC20050
0.9172	High Similarity	NPC306267
0.9137	High Similarity	NPC178054
0.911	High Similarity	NPC46335
0.9103	High Similarity	NPC59692
0.9085	High Similarity	NPC215678
0.9085	High Similarity	NPC274454
0.9051	High Similarity	NPC125579
0.9044	High Similarity	NPC92805
0.9021	High Similarity	NPC174251
0.9021	High Similarity	NPC153182
0.8986	High Similarity	NPC262585
0.8986	High Similarity	NPC20829
0.8986	High Similarity	NPC18189
0.8978	High Similarity	NPC124085
0.8978	High Similarity	NPC117048
0.8955	High Similarity	NPC53986
0.8955	High Similarity	NPC38664
0.8955	High Similarity	NPC274717
0.8929	High Similarity	NPC262189
0.8926	High Similarity	NPC4809
0.8926	High Similarity	NPC73517
0.8926	High Similarity	NPC147743
0.8921	High Similarity	NPC474687
0.8905	High Similarity	NPC85435
0.8905	High Similarity	NPC77196
0.8897	High Similarity	NPC207892
0.8897	High Similarity	NPC300875
0.8897	High Similarity	NPC17343
0.8897	High Similarity	NPC164804
0.8897	High Similarity	NPC196765
0.8897	High Similarity	NPC206224
0.8897	High Similarity	NPC150011
0.8897	High Similarity	NPC118114
0.8897	High Similarity	NPC129106
0.8897	High Similarity	NPC164574
0.8897	High Similarity	NPC293203
0.8897	High Similarity	NPC280653
0.8897	High Similarity	NPC211413
0.8897	High Similarity	NPC268917
0.8897	High Similarity	NPC129784
0.8897	High Similarity	NPC236014
0.8897	High Similarity	NPC228369
0.8897	High Similarity	NPC118683
0.8897	High Similarity	NPC12875
0.8897	High Similarity	NPC476166
0.8897	High Similarity	NPC68205
0.8897	High Similarity	NPC244888
0.8889	High Similarity	NPC93962
0.8872	High Similarity	NPC167571
0.8872	High Similarity	NPC278552
0.8872	High Similarity	NPC207179
0.8867	High Similarity	NPC471404
0.8867	High Similarity	NPC151474
0.8867	High Similarity	NPC205613
0.8867	High Similarity	NPC86630
0.8867	High Similarity	NPC185231
0.8867	High Similarity	NPC159526
0.8867	High Similarity	NPC106601
0.8867	High Similarity	NPC212614
0.8849	High Similarity	NPC141717
0.8849	High Similarity	NPC3049
0.8844	High Similarity	NPC233467
0.8841	High Similarity	NPC473107
0.8841	High Similarity	NPC296915
0.8841	High Similarity	NPC223008
0.8841	High Similarity	NPC198154
0.8841	High Similarity	NPC115335
0.8841	High Similarity	NPC225696
0.8841	High Similarity	NPC97834
0.8832	High Similarity	NPC13005
0.8828	High Similarity	NPC281549
0.8824	High Similarity	NPC470225
0.8824	High Similarity	NPC27187
0.8819	High Similarity	NPC14468
0.8819	High Similarity	NPC260397
0.8815	High Similarity	NPC222572
0.8815	High Similarity	NPC87224
0.8811	High Similarity	NPC15659
0.8811	High Similarity	NPC304894
0.8811	High Similarity	NPC225445
0.8811	High Similarity	NPC473108
0.8806	High Similarity	NPC230479
0.8806	High Similarity	NPC276212
0.8806	High Similarity	NPC283049
0.8806	High Similarity	NPC50315
0.8806	High Similarity	NPC26879
0.8803	High Similarity	NPC230718
0.8803	High Similarity	NPC5253
0.8803	High Similarity	NPC49542
0.8803	High Similarity	NPC139976
0.8803	High Similarity	NPC84207
0.8803	High Similarity	NPC472353
0.8803	High Similarity	NPC128337
0.8794	High Similarity	NPC182509
0.8794	High Similarity	NPC174787
0.8794	High Similarity	NPC22317
0.8794	High Similarity	NPC213607
0.8786	High Similarity	NPC474390
0.8786	High Similarity	NPC87777
0.8786	High Similarity	NPC262328
0.8777	High Similarity	NPC11727
0.8777	High Similarity	NPC15109
0.8767	High Similarity	NPC321657
0.8767	High Similarity	NPC318373
0.8759	High Similarity	NPC162801
0.8759	High Similarity	NPC181497
0.8759	High Similarity	NPC271945
0.875	High Similarity	NPC181615
0.8741	High Similarity	NPC173203
0.8741	High Similarity	NPC116922
0.8741	High Similarity	NPC163508
0.8732	High Similarity	NPC108674
0.8731	High Similarity	NPC103420
0.8731	High Similarity	NPC17809
0.8731	High Similarity	NPC188022
0.8731	High Similarity	NPC102540
0.8731	High Similarity	NPC285040
0.8725	High Similarity	NPC157333
0.8723	High Similarity	NPC260741
0.8723	High Similarity	NPC70682
0.8716	High Similarity	NPC325860
0.8714	High Similarity	NPC470802
0.8705	High Similarity	NPC184269
0.8699	High Similarity	NPC329836
0.8693	High Similarity	NPC12326
0.8681	High Similarity	NPC177597
0.8676	High Similarity	NPC39064
0.8676	High Similarity	NPC47283
0.8671	High Similarity	NPC2613
0.8671	High Similarity	NPC59841
0.8671	High Similarity	NPC204347
0.8671	High Similarity	NPC475891
0.8667	High Similarity	NPC262573
0.8667	High Similarity	NPC471215
0.8662	High Similarity	NPC266197
0.8662	High Similarity	NPC20520
0.8662	High Similarity	NPC291101
0.8662	High Similarity	NPC61783
0.8657	High Similarity	NPC197351
0.8657	High Similarity	NPC134195
0.8657	High Similarity	NPC86502
0.8657	High Similarity	NPC246648
0.8657	High Similarity	NPC106914
0.8652	High Similarity	NPC211549
0.8652	High Similarity	NPC48956
0.8649	High Similarity	NPC329343
0.8649	High Similarity	NPC324517
0.8649	High Similarity	NPC321972
0.8643	High Similarity	NPC473413
0.8643	High Similarity	NPC164787
0.8643	High Similarity	NPC79957
0.8643	High Similarity	NPC61946
0.8639	High Similarity	NPC476969
0.8636	High Similarity	NPC63438
0.863	High Similarity	NPC474397

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 NPC277331 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	852
0.2-0.3	1885
0.3-0.4	2681
0.4-0.5	1639
0.5-0.6	969
0.6-0.7	600
0.7-0.8	105
0.8-0.85	3
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9104	High Similarity	NPD4907	Clinical (unspecified phase)
0.8955	High Similarity	NPD4908	Phase 1
0.8571	High Similarity	NPD1610	Phase 2
0.8561	High Similarity	NPD1613	Approved
0.8561	High Similarity	NPD1612	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD8455	Phase 2
0.8201	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD1548	Phase 1
0.8085	Intermediate Similarity	NPD3027	Phase 3
0.8071	Intermediate Similarity	NPD2861	Phase 2
0.8039	Intermediate Similarity	NPD4380	Phase 2
0.7958	Intermediate Similarity	NPD4625	Phase 3
0.7949	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6959	Discontinued
0.7902	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6166	Phase 2
0.7888	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD7212	Phase 2
0.7881	Intermediate Similarity	NPD7213	Phase 3
0.7862	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD5124	Phase 1
0.7852	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7447	Phase 1
0.7786	Intermediate Similarity	NPD4749	Approved
0.7785	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1091	Approved
0.7758	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD4538	Approved
0.7755	Intermediate Similarity	NPD4536	Approved
0.7755	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD8651	Approved
0.7703	Intermediate Similarity	NPD5960	Phase 3
0.7703	Intermediate Similarity	NPD5588	Approved
0.7673	Intermediate Similarity	NPD7768	Phase 2
0.7671	Intermediate Similarity	NPD4060	Phase 1
0.7669	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD7097	Phase 1
0.7625	Intermediate Similarity	NPD7075	Discontinued
0.7616	Intermediate Similarity	NPD6674	Discontinued
0.7576	Intermediate Similarity	NPD7228	Approved
0.7532	Intermediate Similarity	NPD7411	Suspended
0.753	Intermediate Similarity	NPD5844	Phase 1
0.7518	Intermediate Similarity	NPD7157	Approved
0.7515	Intermediate Similarity	NPD8313	Approved
0.7515	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD5846	Approved
0.75	Intermediate Similarity	NPD6516	Phase 2
0.75	Intermediate Similarity	NPD1652	Phase 2
0.7485	Intermediate Similarity	NPD7074	Phase 3
0.7484	Intermediate Similarity	NPD1934	Approved
0.7484	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5058	Phase 3
0.7452	Intermediate Similarity	NPD1653	Approved
0.7451	Intermediate Similarity	NPD7466	Approved
0.7438	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1549	Phase 2
0.7426	Intermediate Similarity	NPD7843	Approved
0.7425	Intermediate Similarity	NPD7054	Approved
0.7421	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6798	Discontinued
0.7396	Intermediate Similarity	NPD6559	Discontinued
0.7388	Intermediate Similarity	NPD2684	Approved
0.7381	Intermediate Similarity	NPD7472	Approved
0.7379	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7199	Phase 2
0.7375	Intermediate Similarity	NPD37	Approved
0.7375	Intermediate Similarity	NPD6801	Discontinued
0.7362	Intermediate Similarity	NPD6234	Discontinued
0.7346	Intermediate Similarity	NPD4966	Approved
0.7346	Intermediate Similarity	NPD4967	Phase 2
0.7346	Intermediate Similarity	NPD4965	Approved
0.7338	Intermediate Similarity	NPD3750	Approved
0.7337	Intermediate Similarity	NPD6797	Phase 2
0.7333	Intermediate Similarity	NPD3787	Discontinued
0.732	Intermediate Similarity	NPD2424	Discontinued
0.7317	Intermediate Similarity	NPD5494	Approved
0.7313	Intermediate Similarity	NPD290	Approved
0.7294	Intermediate Similarity	NPD7251	Discontinued
0.7292	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5403	Approved
0.7273	Intermediate Similarity	NPD422	Phase 1
0.7267	Intermediate Similarity	NPD8053	Approved
0.7267	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD8054	Approved
0.7267	Intermediate Similarity	NPD5735	Approved
0.7251	Intermediate Similarity	NPD7808	Phase 3
0.7248	Intermediate Similarity	NPD6233	Phase 2
0.7226	Intermediate Similarity	NPD4535	Phase 3
0.7226	Intermediate Similarity	NPD3892	Phase 2
0.7222	Intermediate Similarity	NPD7819	Suspended
0.7211	Intermediate Similarity	NPD3018	Phase 2
0.72	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7041	Phase 2
0.7193	Intermediate Similarity	NPD7240	Approved
0.719	Intermediate Similarity	NPD6099	Approved
0.719	Intermediate Similarity	NPD6100	Approved
0.7188	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5402	Approved
0.7172	Intermediate Similarity	NPD6582	Phase 2
0.7172	Intermediate Similarity	NPD6583	Phase 3
0.7161	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3818	Discontinued
0.7152	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5401	Approved
0.7151	Intermediate Similarity	NPD7549	Discontinued
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD6671	Approved
0.7143	Intermediate Similarity	NPD6584	Phase 3
0.7143	Intermediate Similarity	NPD7266	Discontinued
0.7143	Intermediate Similarity	NPD5763	Approved
0.7126	Intermediate Similarity	NPD7229	Phase 3
0.7126	Intermediate Similarity	NPD6232	Discontinued
0.7124	Intermediate Similarity	NPD1510	Phase 2
0.7117	Intermediate Similarity	NPD1465	Phase 2
0.7117	Intermediate Similarity	NPD2801	Approved
0.7115	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4628	Phase 3
0.7111	Intermediate Similarity	NPD968	Approved
0.7101	Intermediate Similarity	NPD7473	Discontinued
0.7099	Intermediate Similarity	NPD6072	Discontinued
0.7097	Intermediate Similarity	NPD7037	Approved
0.7091	Intermediate Similarity	NPD3749	Approved
0.7089	Intermediate Similarity	NPD1511	Approved
0.7086	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3620	Phase 2
0.7081	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2796	Approved
0.7059	Intermediate Similarity	NPD3751	Discontinued
0.7055	Intermediate Similarity	NPD2982	Phase 2
0.7055	Intermediate Similarity	NPD2983	Phase 2
0.7052	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5061	Approved
0.7051	Intermediate Similarity	NPD5062	Approved
0.7044	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6004	Phase 3
0.7032	Intermediate Similarity	NPD6002	Phase 3
0.7032	Intermediate Similarity	NPD6005	Phase 3
0.7025	Intermediate Similarity	NPD6666	Approved
0.7025	Intermediate Similarity	NPD6667	Approved
0.7018	Intermediate Similarity	NPD8156	Discontinued
0.7014	Intermediate Similarity	NPD5125	Phase 3
0.7014	Intermediate Similarity	NPD5126	Approved
0.7013	Intermediate Similarity	NPD7033	Discontinued
0.7013	Intermediate Similarity	NPD3748	Approved
0.7	Intermediate Similarity	NPD7095	Approved
0.7	Intermediate Similarity	NPD1512	Approved
0.7	Intermediate Similarity	NPD5283	Phase 1
0.6986	Remote Similarity	NPD2981	Phase 2
0.6981	Remote Similarity	NPD6799	Approved
0.6974	Remote Similarity	NPD4140	Approved
0.6974	Remote Similarity	NPD2238	Phase 2
0.697	Remote Similarity	NPD3817	Phase 2
0.6962	Remote Similarity	NPD2677	Approved
0.6959	Remote Similarity	NPD3094	Phase 2
0.6959	Remote Similarity	NPD8099	Discontinued
0.6959	Remote Similarity	NPD8251	Approved
0.6959	Remote Similarity	NPD2797	Approved
0.6959	Remote Similarity	NPD8252	Approved
0.6954	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2200	Suspended
0.6948	Remote Similarity	NPD7119	Phase 2
0.694	Remote Similarity	NPD940	Approved
0.694	Remote Similarity	NPD846	Approved
0.6939	Remote Similarity	NPD5327	Phase 3
0.6933	Remote Similarity	NPD6599	Discontinued
0.6929	Remote Similarity	NPD5535	Approved
0.6928	Remote Similarity	NPD3882	Suspended
0.6928	Remote Similarity	NPD4340	Discontinued
0.6927	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7030	Discontinued
0.6923	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3122	Phase 3
0.6913	Remote Similarity	NPD3690	Phase 2
0.6913	Remote Similarity	NPD3691	Phase 2
0.6903	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7003	Approved
0.6893	Remote Similarity	NPD4663	Approved
0.6892	Remote Similarity	NPD6696	Suspended
0.6892	Remote Similarity	NPD3225	Approved
0.6886	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4097	Suspended
0.6879	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7741	Discontinued
0.6875	Remote Similarity	NPD7390	Discontinued
0.6871	Remote Similarity	NPD7458	Discontinued

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