NPASS Compound

Structure

NPC470828 OpenBabel07101719162D 58 62 0 0 1 0 0 0 0 0999 V2000 -8.7078 -5.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 0.9889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4398 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 -4.2072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 -3.3412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3059 -3.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3059 -4.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 -5.0733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5738 -3.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 -2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7078 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 -2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4398 -2.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.4398 -4.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5738 -4.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7078 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5738 -1.4067 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.2437 1.0933 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -10.4398 -1.9067 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.1097 1.5933 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7078 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 -5.9393 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5032 -1.7614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7078 -2.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4398 -5.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3059 -1.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7078 -4.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 0.1229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 -1.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5738 1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5738 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 1.5933 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 50 1 0 0 0 0 2 51 1 0 0 0 0 3 52 1 0 0 0 0 4 53 1 0 0 0 0 5 54 1 0 0 0 0 6 55 1 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 22 1 0 0 0 0 9 10 2 0 0 0 0 9 23 1 0 0 0 0 10 28 1 0 0 0 0 11 43 2 0 0 0 0 12 22 2 0 0 0 0 12 26 1 0 0 0 0 13 22 1 0 0 0 0 13 30 2 0 0 0 0 14 23 2 0 0 0 0 14 29 1 0 0 0 0 15 24 2 0 0 0 0 15 31 1 0 0 0 0 16 24 1 0 0 0 0 16 32 2 0 0 0 0 17 25 2 0 0 0 0 17 33 1 0 0 0 0 18 25 1 0 0 0 0 18 34 2 0 0 0 0 19 44 1 0 0 0 0 20 35 1 0 0 0 0 20 45 1 0 0 0 0 21 36 1 0 0 0 0 21 46 1 0 0 0 0 23 37 1 0 0 0 0 24 38 1 0 0 0 0 26 27 1 0 0 0 0 26 40 2 0 0 0 0 27 19 1 1 0 0 0 27 39 1 0 0 0 0 28 29 2 0 0 0 0 28 47 1 0 0 0 0 29 50 1 0 0 0 0 30 40 1 0 0 0 0 30 51 1 0 0 0 0 31 41 2 0 0 0 0 31 52 1 0 0 0 0 32 41 1 0 0 0 0 32 53 1 0 0 0 0 33 42 2 0 0 0 0 33 54 1 0 0 0 0 34 42 1 0 0 0 0 34 55 1 0 0 0 0 35 37 1 0 0 0 0 35 56 1 0 0 0 0 36 38 1 0 0 0 0 36 57 1 0 0 0 0 37 48 1 0 0 0 0 38 49 1 0 0 0 0 39 25 1 6 0 0 0 39 58 1 0 0 0 0 40 58 1 0 0 0 0 41 56 1 0 0 0 0 42 57 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	808.29
Volume:	795.939
LogP:	1.739
LogD:	2.005
LogS:	-4.474
# Rotatable Bonds:	20
TPSA:	221.52
# H-Bond Aceptor:	16
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.055
Synthetic Accessibility Score:	4.998
Fsp3:	0.357
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.672
MDCK Permeability:	1.9399318262003362e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.624
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.172
Plasma Protein Binding (PPB):	58.875030517578125%
Volume Distribution (VD):	0.557
Pgp-substrate:	65.7569351196289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.158
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.915
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.764
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.657
CYP3A4-inhibitor:	0.699
CYP3A4-substrate:	0.943

ADMET: Excretion

Clearance (CL):	5.125
Half-life (T1/2):	0.391

ADMET: Toxicity

hERG Blockers:	0.201
Human Hepatotoxicity (H-HT):	0.132
Drug-inuced Liver Injury (DILI):	0.136
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.527
Maximum Recommended Daily Dose:	0.763
Skin Sensitization:	0.278
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.011

Download Data

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

Natural Product: NPC470828

Natural Product ID:	NPC470828
*Common Name:**	5''-Methoxy-4''-O-(8-Guaiacylglycerol)Buddlenol A
IUPAC Name:	(E)-3-[(2R,3S)-2-[4-[1-[4-[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3,5-dimethoxyphenyl]-1,3-dihydroxypropan-2-yl]oxy-3,5-dimethoxyphenyl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal
Synonyms:
Standard InCHIKey:	ZCFXYUOLSAFDRL-ZXJVSXSISA-N
Standard InCHI:	InChI=1S/C42H48O16/c1-50-29-14-23(9-10-28(29)47)37(48)35(20-45)56-41-31(52-3)15-24(16-32(41)53-4)38(49)36(21-46)57-42-33(54-5)17-25(18-34(42)55-6)39-27(19-44)26-12-22(8-7-11-43)13-30(51-2)40(26)58-39/h7-18,27,35-39,44-49H,19-21H2,1-6H3/b8-7+/t27-,35?,36?,37?,38?,39+/m1/s1
SMILES:	COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C(=C3)OC)OC(CO)C(C4=CC(=C(C(=C4)OC)OC(CO)C(C5=CC(=C(C=C5)O)OC)O)OC)O)OC)C=CC=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL225532
PubChem CID:	16216401
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792422]
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17343407]
NPO14922	Tarenna attenuata	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	1
Others	4

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	50.3	%	PMID[464145]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	54.7	%	PMID[464145]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	55.2	%	PMID[464145]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	51.0	%	PMID[464145]
NPT1	Others	Radical scavenging activity		IC50	=	127000.0	nM	PMID[464145]

☑ 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 NPC470828 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	439
0.1-0.2	1468
0.2-0.3	3816
0.3-0.4	10043
0.4-0.5	8810
0.5-0.6	3729
0.6-0.7	6266
0.7-0.8	6896
0.8-0.85	978
0.85-0.9	213
0.9-0.95	32
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC470827
0.9667	High Similarity	NPC470769
0.9542	High Similarity	NPC125495
0.9333	High Similarity	NPC473408
0.9281	High Similarity	NPC115203
0.9276	High Similarity	NPC329343
0.9276	High Similarity	NPC321972
0.9276	High Similarity	NPC324517
0.9211	High Similarity	NPC477612
0.92	High Similarity	NPC260397
0.9145	High Similarity	NPC473266
0.9145	High Similarity	NPC470098
0.9145	High Similarity	NPC470826
0.9133	High Similarity	NPC181615
0.9079	High Similarity	NPC20757
0.9079	High Similarity	NPC227516
0.9067	High Similarity	NPC264706
0.9067	High Similarity	NPC284881
0.9067	High Similarity	NPC474444
0.9067	High Similarity	NPC93433
0.902	High Similarity	NPC475250
0.902	High Similarity	NPC211561
0.9013	High Similarity	NPC320671
0.9013	High Similarity	NPC328567
0.9013	High Similarity	NPC327412
0.9013	High Similarity	NPC320970
0.9006	High Similarity	NPC43065
0.8994	High Similarity	NPC478267
0.8974	High Similarity	NPC157333
0.8968	High Similarity	NPC279406
0.8968	High Similarity	NPC226809
0.8957	High Similarity	NPC180768
0.8954	High Similarity	NPC102934
0.8954	High Similarity	NPC252402
0.8947	High Similarity	NPC317053
0.8947	High Similarity	NPC324492
0.891	High Similarity	NPC224161
0.8889	High Similarity	NPC236202
0.8889	High Similarity	NPC59516
0.8889	High Similarity	NPC170103
0.8889	High Similarity	NPC204770
0.8889	High Similarity	NPC82917
0.8889	High Similarity	NPC108811
0.8889	High Similarity	NPC58190
0.8889	High Similarity	NPC202742
0.8889	High Similarity	NPC263940
0.8889	High Similarity	NPC262911
0.8889	High Similarity	NPC294558
0.8889	High Similarity	NPC70409
0.8889	High Similarity	NPC18185
0.8868	High Similarity	NPC478269
0.8867	High Similarity	NPC263261
0.8867	High Similarity	NPC87725
0.8867	High Similarity	NPC470372
0.8854	High Similarity	NPC46335
0.8831	High Similarity	NPC329836
0.8824	High Similarity	NPC96576
0.882	High Similarity	NPC12326
0.8816	High Similarity	NPC114119
0.8816	High Similarity	NPC15659
0.8816	High Similarity	NPC304894
0.8816	High Similarity	NPC471415
0.8816	High Similarity	NPC470097
0.8808	High Similarity	NPC278469
0.8808	High Similarity	NPC193722
0.88	High Similarity	NPC267291
0.88	High Similarity	NPC291101
0.88	High Similarity	NPC22317
0.88	High Similarity	NPC266197
0.8797	High Similarity	NPC202104
0.8758	High Similarity	NPC216916
0.8758	High Similarity	NPC274960
0.8758	High Similarity	NPC473909
0.8758	High Similarity	NPC163898
0.8758	High Similarity	NPC143120
0.875	High Similarity	NPC163508
0.875	High Similarity	NPC173203
0.8742	High Similarity	NPC178054
0.8742	High Similarity	NPC83375
0.8742	High Similarity	NPC224876
0.8733	High Similarity	NPC260842
0.871	High Similarity	NPC281549
0.871	High Similarity	NPC236166
0.8701	High Similarity	NPC40222
0.8701	High Similarity	NPC268515
0.8693	High Similarity	NPC28440
0.8693	High Similarity	NPC171932
0.8693	High Similarity	NPC93323
0.8693	High Similarity	NPC12641
0.8693	High Similarity	NPC45257
0.8693	High Similarity	NPC63879
0.8693	High Similarity	NPC280092
0.8688	High Similarity	NPC73517
0.8688	High Similarity	NPC4809
0.8688	High Similarity	NPC147743
0.8675	High Similarity	NPC309124
0.8675	High Similarity	NPC184797
0.8671	High Similarity	NPC475141
0.8667	High Similarity	NPC477938
0.8667	High Similarity	NPC474390
0.8654	High Similarity	NPC476969
0.8654	High Similarity	NPC318373
0.8654	High Similarity	NPC321657
0.865	High Similarity	NPC45943
0.8645	High Similarity	NPC16269
0.8645	High Similarity	NPC21776
0.8645	High Similarity	NPC101376
0.8642	High Similarity	NPC149873
0.8642	High Similarity	NPC7191
0.8634	High Similarity	NPC212614
0.8634	High Similarity	NPC151474
0.8634	High Similarity	NPC185231
0.8634	High Similarity	NPC159526
0.8634	High Similarity	NPC86630
0.8634	High Similarity	NPC106601
0.8634	High Similarity	NPC205613
0.8634	High Similarity	NPC471404
0.8627	High Similarity	NPC85264
0.8627	High Similarity	NPC47633
0.8627	High Similarity	NPC102044
0.8618	High Similarity	NPC311530
0.8616	High Similarity	NPC473736
0.8616	High Similarity	NPC268484
0.8609	High Similarity	NPC236306
0.8609	High Similarity	NPC473739
0.8609	High Similarity	NPC70682
0.8609	High Similarity	NPC260741
0.8609	High Similarity	NPC232164
0.8609	High Similarity	NPC22517
0.8608	High Similarity	NPC157783
0.8608	High Similarity	NPC46283
0.8608	High Similarity	NPC322899
0.8608	High Similarity	NPC44192
0.8608	High Similarity	NPC469944
0.8608	High Similarity	NPC226108
0.8608	High Similarity	NPC272552
0.8608	High Similarity	NPC134911
0.8608	High Similarity	NPC59692
0.86	High Similarity	NPC29799
0.86	High Similarity	NPC209985
0.86	High Similarity	NPC156502
0.86	High Similarity	NPC77861
0.86	High Similarity	NPC263367
0.86	High Similarity	NPC177160
0.86	High Similarity	NPC477939
0.86	High Similarity	NPC54743
0.86	High Similarity	NPC10737
0.8599	High Similarity	NPC472709
0.8599	High Similarity	NPC472710
0.859	High Similarity	NPC476348
0.859	High Similarity	NPC187398
0.8589	High Similarity	NPC476372
0.8589	High Similarity	NPC476371
0.8571	High Similarity	NPC473108
0.8562	High Similarity	NPC475891
0.8562	High Similarity	NPC67467
0.8562	High Similarity	NPC107161
0.8562	High Similarity	NPC2613
0.8562	High Similarity	NPC59841
0.8562	High Similarity	NPC131971
0.8562	High Similarity	NPC204347
0.8553	High Similarity	NPC160283
0.8553	High Similarity	NPC254759
0.8553	High Similarity	NPC472091
0.8553	High Similarity	NPC472090
0.8553	High Similarity	NPC472092
0.8553	High Similarity	NPC223720
0.8553	High Similarity	NPC262189
0.8553	High Similarity	NPC306267
0.8553	High Similarity	NPC20050
0.8544	High Similarity	NPC2745
0.8544	High Similarity	NPC302915
0.8533	High Similarity	NPC125579
0.8533	High Similarity	NPC93783
0.8528	High Similarity	NPC469889
0.8526	High Similarity	NPC262297
0.8526	High Similarity	NPC476347
0.8519	High Similarity	NPC241600
0.8519	High Similarity	NPC215400
0.8519	High Similarity	NPC230531
0.8519	High Similarity	NPC173726
0.8516	High Similarity	NPC469557
0.8512	High Similarity	NPC98583
0.8509	High Similarity	NPC165483
0.8509	High Similarity	NPC11411
0.8506	High Similarity	NPC477616
0.8503	High Similarity	NPC102277
0.8503	High Similarity	NPC279209
0.85	High Similarity	NPC8712
0.8497	Intermediate Similarity	NPC247291
0.8497	Intermediate Similarity	NPC471389
0.8497	Intermediate Similarity	NPC100482
0.8497	Intermediate Similarity	NPC277331
0.8497	Intermediate Similarity	NPC35216
0.8491	Intermediate Similarity	NPC160196
0.8491	Intermediate Similarity	NPC476391
0.8491	Intermediate Similarity	NPC120774
0.8491	Intermediate Similarity	NPC264875
0.8491	Intermediate Similarity	NPC163598
0.8491	Intermediate Similarity	NPC476434

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 NPC470828 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	902
0.2-0.3	1807
0.3-0.4	2784
0.4-0.5	1722
0.5-0.6	944
0.6-0.7	516
0.7-0.8	103
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8212	Intermediate Similarity	NPD1613	Approved
0.8212	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD3027	Phase 3
0.8079	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6166	Phase 2
0.8023	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD4908	Phase 1
0.7939	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD5844	Phase 1
0.7881	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1934	Approved
0.7857	Intermediate Similarity	NPD6234	Discontinued
0.7853	Intermediate Similarity	NPD1653	Approved
0.7849	Intermediate Similarity	NPD3818	Discontinued
0.7849	Intermediate Similarity	NPD7228	Approved
0.7811	Intermediate Similarity	NPD5494	Approved
0.7784	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6559	Discontinued
0.7771	Intermediate Similarity	NPD37	Approved
0.7765	Intermediate Similarity	NPD7199	Phase 2
0.7759	Intermediate Similarity	NPD7472	Approved
0.7759	Intermediate Similarity	NPD7074	Phase 3
0.7738	Intermediate Similarity	NPD4966	Approved
0.7738	Intermediate Similarity	NPD3882	Suspended
0.7738	Intermediate Similarity	NPD4967	Phase 2
0.7738	Intermediate Similarity	NPD7768	Phase 2
0.7738	Intermediate Similarity	NPD4965	Approved
0.7701	Intermediate Similarity	NPD7054	Approved
0.7661	Intermediate Similarity	NPD8127	Discontinued
0.7651	Intermediate Similarity	NPD4380	Phase 2
0.7627	Intermediate Similarity	NPD7808	Phase 3
0.7619	Intermediate Similarity	NPD8455	Phase 2
0.7619	Intermediate Similarity	NPD2801	Approved
0.7598	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7473	Discontinued
0.7578	Intermediate Similarity	NPD6674	Discontinued
0.7572	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7251	Discontinued
0.7562	Intermediate Similarity	NPD7266	Discontinued
0.7558	Intermediate Similarity	NPD6959	Discontinued
0.7514	Intermediate Similarity	NPD6797	Phase 2
0.7514	Intermediate Similarity	NPD6232	Discontinued
0.7486	Intermediate Similarity	NPD8313	Approved
0.7486	Intermediate Similarity	NPD8312	Approved
0.7485	Intermediate Similarity	NPD7075	Discontinued
0.7483	Intermediate Similarity	NPD1610	Phase 2
0.7473	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD7240	Approved
0.7468	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5124	Phase 1
0.743	Intermediate Similarity	NPD7549	Discontinued
0.7429	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2861	Phase 2
0.7412	Intermediate Similarity	NPD1465	Phase 2
0.7412	Intermediate Similarity	NPD7819	Suspended
0.7405	Intermediate Similarity	NPD4060	Phase 1
0.7401	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1511	Approved
0.7389	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3817	Phase 2
0.7349	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4625	Phase 3
0.731	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1512	Approved
0.7296	Intermediate Similarity	NPD3620	Phase 2
0.7296	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7411	Suspended
0.7273	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8054	Approved
0.7253	Intermediate Similarity	NPD8053	Approved
0.7251	Intermediate Similarity	NPD6801	Discontinued
0.7246	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD8651	Approved
0.7219	Intermediate Similarity	NPD1548	Phase 1
0.7216	Intermediate Similarity	NPD7229	Phase 3
0.7212	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3018	Phase 2
0.7188	Intermediate Similarity	NPD7680	Approved
0.7186	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7685	Pre-registration
0.7174	Intermediate Similarity	NPD8434	Phase 2
0.7169	Intermediate Similarity	NPD6190	Approved
0.7168	Intermediate Similarity	NPD5402	Approved
0.7161	Intermediate Similarity	NPD4749	Approved
0.7159	Intermediate Similarity	NPD1247	Approved
0.7152	Intermediate Similarity	NPD1652	Phase 2
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD919	Approved
0.7135	Intermediate Similarity	NPD7906	Approved
0.7134	Intermediate Similarity	NPD5762	Approved
0.7134	Intermediate Similarity	NPD5763	Approved
0.7108	Intermediate Similarity	NPD3750	Approved
0.7108	Intermediate Similarity	NPD8166	Discontinued
0.7091	Intermediate Similarity	NPD2424	Discontinued
0.7091	Intermediate Similarity	NPD1549	Phase 2
0.7086	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3926	Phase 2
0.7076	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5403	Approved
0.7055	Intermediate Similarity	NPD7097	Phase 1
0.7051	Intermediate Similarity	NPD2982	Phase 2
0.7051	Intermediate Similarity	NPD2983	Phase 2
0.7048	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7447	Phase 1
0.7037	Intermediate Similarity	NPD5735	Approved
0.7037	Intermediate Similarity	NPD6355	Discontinued
0.7032	Intermediate Similarity	NPD422	Phase 1
0.703	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5588	Approved
0.7006	Intermediate Similarity	NPD4628	Phase 3
0.7006	Intermediate Similarity	NPD7466	Approved
0.7	Intermediate Similarity	NPD5283	Phase 1
0.6994	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4663	Approved
0.6989	Remote Similarity	NPD3749	Approved
0.6987	Remote Similarity	NPD2981	Phase 2
0.6982	Remote Similarity	NPD4357	Discontinued
0.6982	Remote Similarity	NPD7213	Phase 3
0.6982	Remote Similarity	NPD7212	Phase 2
0.6977	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2796	Approved
0.697	Remote Similarity	NPD6099	Approved
0.697	Remote Similarity	NPD6100	Approved
0.6961	Remote Similarity	NPD3751	Discontinued
0.6957	Remote Similarity	NPD6798	Discontinued
0.6951	Remote Similarity	NPD4536	Approved
0.6951	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4538	Approved
0.6944	Remote Similarity	NPD2489	Approved
0.6944	Remote Similarity	NPD27	Approved
0.6941	Remote Similarity	NPD5401	Approved
0.6941	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7843	Approved
0.6927	Remote Similarity	NPD3051	Approved
0.6927	Remote Similarity	NPD3787	Discontinued
0.6923	Remote Similarity	NPD5058	Phase 3
0.6923	Remote Similarity	NPD8156	Discontinued
0.6919	Remote Similarity	NPD4578	Approved
0.6919	Remote Similarity	NPD7310	Approved
0.6919	Remote Similarity	NPD7311	Approved
0.6919	Remote Similarity	NPD4577	Approved
0.6919	Remote Similarity	NPD7312	Approved
0.6919	Remote Similarity	NPD7313	Approved
0.6919	Remote Similarity	NPD8151	Discontinued
0.6909	Remote Similarity	NPD1510	Phase 2
0.6908	Remote Similarity	NPD7157	Approved
0.6905	Remote Similarity	NPD6331	Phase 2
0.6901	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6273	Approved
0.6894	Remote Similarity	NPD7095	Approved
0.6889	Remote Similarity	NPD2970	Approved
0.6889	Remote Similarity	NPD2969	Approved
0.6882	Remote Similarity	NPD6799	Approved
0.6882	Remote Similarity	NPD7309	Approved
0.6881	Remote Similarity	NPD7047	Phase 3
0.6875	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4140	Approved
0.6868	Remote Similarity	NPD8099	Discontinued
0.6868	Remote Similarity	NPD8251	Approved
0.6868	Remote Similarity	NPD8252	Approved
0.6867	Remote Similarity	NPD2935	Discontinued
0.6867	Remote Similarity	NPD1551	Phase 2
0.6867	Remote Similarity	NPD228	Approved
0.6862	Remote Similarity	NPD6842	Approved
0.6862	Remote Similarity	NPD6841	Approved
0.6862	Remote Similarity	NPD6843	Phase 3
0.6842	Remote Similarity	NPD2532	Approved
0.6842	Remote Similarity	NPD2534	Approved
0.6842	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2533	Approved
0.6839	Remote Similarity	NPD6599	Discontinued
0.6835	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD230	Phase 1
0.6826	Remote Similarity	NPD6005	Phase 3
0.6826	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6004	Phase 3
0.6826	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6002	Phase 3
0.6826	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5536	Phase 2
0.6815	Remote Similarity	NPD3705	Approved
0.6815	Remote Similarity	NPD1091	Approved
0.681	Remote Similarity	NPD6233	Phase 2
0.6807	Remote Similarity	NPD5960	Phase 3

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