NPASS Compound

Structure

CID304322 OpenBabel06191716112D 60 66 0 0 1 0 0 0 0 0999 V2000 -1.3666 5.7496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0347 4.7316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3173 -1.0484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7186 -0.0304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5327 4.4934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6917 3.2062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1352 -3.4995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1533 -4.9008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5477 4.0271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8997 -1.7529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9975 2.8461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8577 -3.3185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5422 4.1316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4929 -2.6665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2054 1.8679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7532 -2.3239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7232 2.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9106 -1.9620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0240 -0.1395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0126 -1.1037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7123 2.6181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0971 -3.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9270 -2.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9599 4.8361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3119 -0.9439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7407 3.5152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0487 -3.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1300 3.3226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4984 -2.7710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4623 1.1988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8397 -1.9172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9270 -0.4485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3110 1.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9161 -2.0665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8216 -0.5160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2319 0.8387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3338 -1.3620 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1245 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0917 -3.6846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3055 1.7046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1171 -2.0983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5094 -2.9801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9261 0.4786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5112 1.5078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0307 -2.5050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1830 1.1477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6702 0.2206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7351 -0.9227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3283 -1.2575 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9043 0.6865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5312 4.3407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6794 -4.4936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8933 0.8955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3081 -2.6860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3033 2.4860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1352 -3.4995 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3909 2.1258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5148 -3.0846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -0.2794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4043 -0.1795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 27 1 0 0 0 0 9 13 1 0 0 0 0 9 24 2 0 0 0 0 10 14 1 0 0 0 0 10 25 2 0 0 0 0 11 15 1 0 0 0 0 11 26 2 0 0 0 0 12 16 1 0 0 0 0 12 27 2 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 31 1 0 0 0 0 17 28 2 0 0 0 0 17 33 1 0 0 0 0 18 29 2 0 0 0 0 18 34 1 0 0 0 0 19 32 2 0 0 0 0 19 36 1 0 0 0 0 20 35 1 0 0 0 0 20 41 2 0 0 0 0 21 38 2 0 0 0 0 21 40 1 0 0 0 0 22 39 2 0 0 0 0 22 42 1 0 0 0 0 23 58 1 0 0 0 0 28 38 1 0 0 0 0 29 39 1 0 0 0 0 30 44 1 0 0 0 0 30 47 2 0 0 0 0 31 45 2 0 0 0 0 31 48 1 0 0 0 0 32 37 1 0 0 0 0 32 47 1 0 0 0 0 33 40 2 0 0 0 0 33 50 1 0 0 0 0 34 42 2 0 0 0 0 35 43 1 0 0 0 0 35 48 2 0 0 0 0 36 44 2 0 0 0 0 36 46 1 0 0 0 0 37 23 1 1 0 0 0 37 49 1 0 0 0 0 38 51 1 0 0 0 0 39 52 1 0 0 0 0 40 53 1 0 0 0 0 41 45 1 0 0 0 0 41 54 1 0 0 0 0 42 58 1 0 0 0 0 43 46 1 0 0 0 0 43 50 2 0 0 0 0 44 55 1 0 0 0 0 45 56 1 0 0 0 0 46 57 2 0 0 0 0 47 59 1 0 0 0 0 48 60 1 0 0 0 0 49 34 1 1 0 0 0 49 59 1 0 0 0 0 50 60 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	812.36
Volume:	853.907
LogP:	11.323
LogD:	5.289
LogS:	-1.844
# Rotatable Bonds:	11
TPSA:	170.05
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.043
Synthetic Accessibility Score:	5.031
Fsp3:	0.3
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.965
MDCK Permeability:	1.1173007806064561e-05
Pgp-inhibitor:	0.888
Pgp-substrate:	0.939
Human Intestinal Absorption (HIA):	0.631
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	106.2026138305664%
Volume Distribution (VD):	0.772
Pgp-substrate:	12.636406898498535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.196
CYP2C19-inhibitor:	0.818
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.609
CYP2C9-substrate:	0.627
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.076
CYP3A4-substrate:	0.122

ADMET: Excretion

Clearance (CL):	12.615
Half-life (T1/2):	0.014

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.995
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.258
Rat Oral Acute Toxicity:	0.909
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.932
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.877
Respiratory Toxicity:	0.04

Download Data

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

Natural Product: NPC304322

Natural Product ID:	NPC304322
*Common Name:**	Lespeflorin J3
IUPAC Name:	[(6aR,11aR)-3,9-dihydroxy-2,10-bis(3-methylbut-2-enyl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-8-yl]-[2-[2,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5,6-dihydroxy-7-(3-methylbut-2-enyl)-1-benzofuran-3-yl]methanone
Synonyms:	Lespeflorin J3
Standard InCHIKey:	BEZJLLIBPJHWLI-HNKXTRRSSA-N
Standard InCHI:	InChI=1S/C50H52O10/c1-24(2)9-13-28-17-33(40(53)21-38(28)51)50-43(35-20-41(54)45(56)31(48(35)60-50)16-12-27(7)8)46(57)36-19-32-37-23-58-42-22-39(52)29(14-10-25(3)4)18-34(42)49(37)59-47(32)30(44(36)55)15-11-26(5)6/h9-12,17-22,37,49,51-56H,13-16,23H2,1-8H3/t37-,49-/m0/s1
SMILES:	CC(=CCc1c2O[C@@H]3[C@H](c2cc(c1O)C(=O)c1c(oc2c1cc(O)c(c2CC=C(C)C)O)c1cc(CC=C(C)C)c(cc1O)O)COc1c3cc(CC=C(C)C)c(c1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL557191
PubChem CID:	25243394
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
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19102656]
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[19132934]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10080	Teucrium betonicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13293	Lespedeza floribunda	Species	Fabaceae	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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	37700.0	nM	PMID[470837]

☑ 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 NPC304322 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	464
0.1-0.2	1727
0.2-0.3	3676
0.3-0.4	9610
0.4-0.5	9292
0.5-0.6	3958
0.6-0.7	5453
0.7-0.8	5219
0.8-0.85	2439
0.85-0.9	816
0.9-0.95	39
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9941	High Similarity	NPC139683
0.9941	High Similarity	NPC73929
0.9941	High Similarity	NPC47905
0.92	High Similarity	NPC150977
0.9176	High Similarity	NPC50394
0.9172	High Similarity	NPC37183
0.9128	High Similarity	NPC248593
0.9128	High Similarity	NPC174700
0.9128	High Similarity	NPC28589
0.9118	High Similarity	NPC277480
0.9086	High Similarity	NPC185275
0.9029	High Similarity	NPC475783
0.9029	High Similarity	NPC471789
0.9029	High Similarity	NPC265380
0.9012	High Similarity	NPC53252
0.9006	High Similarity	NPC320741
0.9006	High Similarity	NPC171985
0.9006	High Similarity	NPC224851
0.9	High Similarity	NPC38591
0.8977	High Similarity	NPC324742
0.8966	High Similarity	NPC473834
0.8966	High Similarity	NPC261471
0.8966	High Similarity	NPC310794
0.8966	High Similarity	NPC37606
0.896	High Similarity	NPC218533
0.896	High Similarity	NPC78830
0.8947	High Similarity	NPC291110
0.8941	High Similarity	NPC473012
0.8914	High Similarity	NPC300657
0.8902	High Similarity	NPC107627
0.8895	High Similarity	NPC251336
0.8889	High Similarity	NPC472278
0.8889	High Similarity	NPC473313
0.8889	High Similarity	NPC473009
0.8889	High Similarity	NPC329669
0.8882	High Similarity	NPC301256
0.8882	High Similarity	NPC312273
0.8864	High Similarity	NPC156955
0.8864	High Similarity	NPC164384
0.8857	High Similarity	NPC149846
0.8851	High Similarity	NPC131866
0.8844	High Similarity	NPC253730
0.8844	High Similarity	NPC86477
0.8844	High Similarity	NPC286230
0.8844	High Similarity	NPC247973
0.8837	High Similarity	NPC259757
0.8837	High Similarity	NPC473010
0.88	High Similarity	NPC472454
0.88	High Similarity	NPC186847
0.88	High Similarity	NPC257667
0.8793	High Similarity	NPC300307
0.8793	High Similarity	NPC475212
0.8786	High Similarity	NPC272560
0.8779	High Similarity	NPC273959
0.8765	High Similarity	NPC40583
0.8757	High Similarity	NPC216307
0.8757	High Similarity	NPC8127
0.8757	High Similarity	NPC49667
0.875	High Similarity	NPC117450
0.8743	High Similarity	NPC279209
0.8743	High Similarity	NPC476365
0.8743	High Similarity	NPC180768
0.8743	High Similarity	NPC102277
0.8736	High Similarity	NPC14662
0.8736	High Similarity	NPC243877
0.8728	High Similarity	NPC169471
0.8728	High Similarity	NPC300053
0.8728	High Similarity	NPC473286
0.8728	High Similarity	NPC39306
0.8728	High Similarity	NPC326520
0.8728	High Similarity	NPC477840
0.8721	High Similarity	NPC312056
0.8721	High Similarity	NPC81679
0.8721	High Similarity	NPC220912
0.8721	High Similarity	NPC84515
0.8715	High Similarity	NPC97523
0.8713	High Similarity	NPC304839
0.8713	High Similarity	NPC220582
0.8701	High Similarity	NPC99591
0.8701	High Similarity	NPC287243
0.8698	High Similarity	NPC113906
0.8693	High Similarity	NPC212038
0.8693	High Similarity	NPC271848
0.8693	High Similarity	NPC81332
0.8693	High Similarity	NPC262580
0.8693	High Similarity	NPC4200
0.8693	High Similarity	NPC289396
0.8693	High Similarity	NPC307286
0.8693	High Similarity	NPC100251
0.8681	High Similarity	NPC473618
0.8678	High Similarity	NPC119589
0.8678	High Similarity	NPC170245
0.8678	High Similarity	NPC173292
0.8678	High Similarity	NPC53640
0.8678	High Similarity	NPC128293
0.8671	High Similarity	NPC18100
0.8671	High Similarity	NPC133065
0.8667	High Similarity	NPC471842
0.8663	High Similarity	NPC45124
0.8663	High Similarity	NPC228383
0.8663	High Similarity	NPC472275
0.8663	High Similarity	NPC142252
0.8663	High Similarity	NPC266314
0.8663	High Similarity	NPC188486
0.8663	High Similarity	NPC30655
0.8663	High Similarity	NPC74854
0.8659	High Similarity	NPC473785
0.8655	High Similarity	NPC469658
0.8655	High Similarity	NPC15815
0.8655	High Similarity	NPC196879
0.8652	High Similarity	NPC478050
0.8652	High Similarity	NPC471841
0.8652	High Similarity	NPC101991
0.8644	High Similarity	NPC82217
0.8644	High Similarity	NPC216842
0.8644	High Similarity	NPC476640
0.8644	High Similarity	NPC98583
0.8644	High Similarity	NPC65885
0.8639	High Similarity	NPC298692
0.8636	High Similarity	NPC472276
0.8636	High Similarity	NPC103307
0.8636	High Similarity	NPC120220
0.8629	High Similarity	NPC476459
0.8629	High Similarity	NPC260266
0.8626	High Similarity	NPC179947
0.8621	High Similarity	NPC472277
0.8621	High Similarity	NPC29411
0.8619	High Similarity	NPC154527
0.8613	High Similarity	NPC476247
0.8613	High Similarity	NPC219927
0.8613	High Similarity	NPC473011
0.8613	High Similarity	NPC477841
0.8611	High Similarity	NPC47883
0.8611	High Similarity	NPC117668
0.8605	High Similarity	NPC98023
0.8605	High Similarity	NPC195136
0.8605	High Similarity	NPC188967
0.8605	High Similarity	NPC226462
0.8603	High Similarity	NPC207467
0.8603	High Similarity	NPC246877
0.8596	High Similarity	NPC236796
0.8596	High Similarity	NPC289244
0.8596	High Similarity	NPC271741
0.8596	High Similarity	NPC262286
0.8596	High Similarity	NPC227906
0.8596	High Similarity	NPC36852
0.8596	High Similarity	NPC469584
0.8596	High Similarity	NPC287789
0.8596	High Similarity	NPC223787
0.8596	High Similarity	NPC1796
0.8596	High Similarity	NPC257166
0.8588	High Similarity	NPC230619
0.8588	High Similarity	NPC477836
0.8588	High Similarity	NPC79375
0.8588	High Similarity	NPC65333
0.8588	High Similarity	NPC54098
0.8588	High Similarity	NPC121333
0.8588	High Similarity	NPC37253
0.8588	High Similarity	NPC472584
0.8588	High Similarity	NPC477529
0.8587	High Similarity	NPC264302
0.858	High Similarity	NPC125300
0.858	High Similarity	NPC152477
0.858	High Similarity	NPC242395
0.858	High Similarity	NPC211309
0.858	High Similarity	NPC106976
0.858	High Similarity	NPC5871
0.858	High Similarity	NPC288813
0.8571	High Similarity	NPC207575
0.8571	High Similarity	NPC43065
0.8571	High Similarity	NPC112380
0.8571	High Similarity	NPC120593
0.8571	High Similarity	NPC226725
0.8571	High Similarity	NPC235610
0.8571	High Similarity	NPC13481
0.8571	High Similarity	NPC82330
0.8564	High Similarity	NPC321916
0.8564	High Similarity	NPC132111
0.8563	High Similarity	NPC7483
0.8563	High Similarity	NPC472281
0.8563	High Similarity	NPC272064
0.8563	High Similarity	NPC205265
0.8563	High Similarity	NPC159508
0.8563	High Similarity	NPC475985
0.8563	High Similarity	NPC41301
0.8563	High Similarity	NPC124038
0.8556	High Similarity	NPC121888
0.8556	High Similarity	NPC183843
0.8555	High Similarity	NPC471211
0.8555	High Similarity	NPC475883
0.8555	High Similarity	NPC231758
0.8555	High Similarity	NPC158188
0.8555	High Similarity	NPC40491
0.8555	High Similarity	NPC474351
0.8555	High Similarity	NPC474186
0.8555	High Similarity	NPC471212
0.8555	High Similarity	NPC134783
0.8555	High Similarity	NPC278052
0.8547	High Similarity	NPC95936
0.8547	High Similarity	NPC329091

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 NPC304322 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	943
0.2-0.3	1896
0.3-0.4	2704
0.4-0.5	1842
0.5-0.6	892
0.6-0.7	308
0.7-0.8	125
0.8-0.85	33
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8529	High Similarity	NPD2393	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD5494	Approved
0.8448	Intermediate Similarity	NPD6959	Discontinued
0.8409	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD6166	Phase 2
0.8372	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD1934	Approved
0.8208	Intermediate Similarity	NPD2801	Approved
0.8202	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD7473	Discontinued
0.8122	Intermediate Similarity	NPD7074	Phase 3
0.8118	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD3882	Suspended
0.8111	Intermediate Similarity	NPD3818	Discontinued
0.8066	Intermediate Similarity	NPD5844	Phase 1
0.8066	Intermediate Similarity	NPD7054	Approved
0.8035	Intermediate Similarity	NPD4380	Phase 2
0.8033	Intermediate Similarity	NPD6559	Discontinued
0.8022	Intermediate Similarity	NPD7472	Approved
0.8011	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD7819	Suspended
0.7989	Intermediate Similarity	NPD6232	Discontinued
0.7966	Intermediate Similarity	NPD7075	Discontinued
0.7966	Intermediate Similarity	NPD3749	Approved
0.7944	Intermediate Similarity	NPD3926	Phase 2
0.7935	Intermediate Similarity	NPD7251	Discontinued
0.7895	Intermediate Similarity	NPD1511	Approved
0.7892	Intermediate Similarity	NPD7808	Phase 3
0.7892	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7411	Suspended
0.788	Intermediate Similarity	NPD6797	Phase 2
0.7869	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD1247	Approved
0.7803	Intermediate Similarity	NPD1512	Approved
0.7797	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD8312	Approved
0.7754	Intermediate Similarity	NPD8313	Approved
0.7746	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD7228	Approved
0.7706	Intermediate Similarity	NPD1549	Phase 2
0.7697	Intermediate Similarity	NPD1465	Phase 2
0.7654	Intermediate Similarity	NPD3817	Phase 2
0.7647	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2344	Approved
0.7624	Intermediate Similarity	NPD6234	Discontinued
0.7612	Intermediate Similarity	NPD8151	Discontinued
0.7586	Intermediate Similarity	NPD7390	Discontinued
0.7558	Intermediate Similarity	NPD2800	Approved
0.7556	Intermediate Similarity	NPD5402	Approved
0.7543	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6801	Discontinued
0.7539	Intermediate Similarity	NPD8434	Phase 2
0.7527	Intermediate Similarity	NPD919	Approved
0.7485	Intermediate Similarity	NPD2796	Approved
0.7471	Intermediate Similarity	NPD2309	Approved
0.7458	Intermediate Similarity	NPD920	Approved
0.7443	Intermediate Similarity	NPD2534	Approved
0.7443	Intermediate Similarity	NPD2533	Approved
0.7443	Intermediate Similarity	NPD2532	Approved
0.7433	Intermediate Similarity	NPD3751	Discontinued
0.7427	Intermediate Similarity	NPD1510	Phase 2
0.7418	Intermediate Similarity	NPD4967	Phase 2
0.7418	Intermediate Similarity	NPD4966	Approved
0.7418	Intermediate Similarity	NPD4965	Approved
0.7413	Intermediate Similarity	NPD7871	Phase 2
0.7413	Intermediate Similarity	NPD7870	Phase 2
0.7387	Intermediate Similarity	NPD6778	Approved
0.7387	Intermediate Similarity	NPD6781	Approved
0.7387	Intermediate Similarity	NPD6779	Approved
0.7387	Intermediate Similarity	NPD6776	Approved
0.7387	Intermediate Similarity	NPD6780	Approved
0.7387	Intermediate Similarity	NPD6777	Approved
0.7387	Intermediate Similarity	NPD6782	Approved
0.7363	Intermediate Similarity	NPD7698	Approved
0.7363	Intermediate Similarity	NPD7435	Discontinued
0.7363	Intermediate Similarity	NPD7696	Phase 3
0.7363	Intermediate Similarity	NPD7697	Approved
0.7358	Intermediate Similarity	NPD8150	Discontinued
0.7356	Intermediate Similarity	NPD1243	Approved
0.7351	Intermediate Similarity	NPD7199	Phase 2
0.7345	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3787	Discontinued
0.7308	Intermediate Similarity	NPD8455	Phase 2
0.7304	Intermediate Similarity	NPD7701	Phase 2
0.7294	Intermediate Similarity	NPD1240	Approved
0.7294	Intermediate Similarity	NPD943	Approved
0.7288	Intermediate Similarity	NPD6799	Approved
0.7283	Intermediate Similarity	NPD2935	Discontinued
0.7282	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7783	Phase 2
0.7282	Intermediate Similarity	NPD7801	Approved
0.7278	Intermediate Similarity	NPD3226	Approved
0.7277	Intermediate Similarity	NPD7240	Approved
0.7273	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD37	Approved
0.7249	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6599	Discontinued
0.7233	Intermediate Similarity	NPD7874	Approved
0.7233	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7229	Phase 3
0.7214	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6651	Approved
0.7209	Intermediate Similarity	NPD1607	Approved
0.72	Intermediate Similarity	NPD7699	Phase 2
0.72	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7700	Phase 2
0.7188	Intermediate Similarity	NPD7685	Pre-registration
0.7176	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5403	Approved
0.7151	Intermediate Similarity	NPD230	Phase 1
0.7151	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6823	Phase 2
0.7136	Intermediate Similarity	NPD6535	Approved
0.7136	Intermediate Similarity	NPD6534	Approved
0.7135	Intermediate Similarity	NPD5953	Discontinued
0.712	Intermediate Similarity	NPD5760	Phase 2
0.712	Intermediate Similarity	NPD5761	Phase 2
0.7119	Intermediate Similarity	NPD3750	Approved
0.7108	Intermediate Similarity	NPD7680	Approved
0.7107	Intermediate Similarity	NPD4287	Approved
0.7093	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1613	Approved
0.7088	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6100	Approved
0.7086	Intermediate Similarity	NPD6099	Approved
0.7059	Intermediate Similarity	NPD4908	Phase 1
0.7056	Intermediate Similarity	NPD5401	Approved
0.7037	Intermediate Similarity	NPD5711	Approved
0.7037	Intermediate Similarity	NPD5710	Approved
0.7031	Intermediate Similarity	NPD7286	Phase 2
0.7029	Intermediate Similarity	NPD2799	Discontinued
0.7022	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7458	Discontinued
0.699	Remote Similarity	NPD8320	Phase 1
0.699	Remote Similarity	NPD8319	Approved
0.6989	Remote Similarity	NPD2296	Approved
0.6984	Remote Similarity	NPD8127	Discontinued
0.6983	Remote Similarity	NPD6190	Approved
0.6977	Remote Similarity	NPD7907	Approved
0.6977	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD4363	Phase 3
0.6965	Remote Similarity	NPD4360	Phase 2
0.6959	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2346	Discontinued
0.694	Remote Similarity	NPD1653	Approved
0.6932	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4628	Phase 3
0.6927	Remote Similarity	NPD8166	Discontinued
0.6915	Remote Similarity	NPD6212	Phase 3
0.6915	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6213	Phase 3
0.6893	Remote Similarity	NPD5404	Approved
0.6893	Remote Similarity	NPD5405	Approved
0.6893	Remote Similarity	NPD5406	Approved
0.6893	Remote Similarity	NPD5408	Approved
0.6893	Remote Similarity	NPD1551	Phase 2
0.6882	Remote Similarity	NPD6280	Approved
0.6882	Remote Similarity	NPD6844	Discontinued
0.6882	Remote Similarity	NPD6279	Approved
0.6879	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6808	Phase 2
0.6854	Remote Similarity	NPD1471	Phase 3
0.6842	Remote Similarity	NPD7584	Approved
0.6836	Remote Similarity	NPD3748	Approved
0.6833	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7003	Approved
0.6828	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3027	Phase 3
0.6818	Remote Similarity	NPD8059	Phase 3
0.6818	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4665	Approved
0.6806	Remote Similarity	NPD4111	Phase 1
0.6804	Remote Similarity	NPD7177	Discontinued
0.6802	Remote Similarity	NPD2861	Phase 2
0.6802	Remote Similarity	NPD7549	Discontinued
0.6782	Remote Similarity	NPD2313	Discontinued
0.6765	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4361	Phase 2
0.6761	Remote Similarity	NPD447	Suspended
0.6748	Remote Similarity	NPD8285	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