NPASS Compound

Structure

CID258474 OpenBabel06191716062D 40 45 0 0 1 0 0 0 0 0999 V2000 -0.8472 -3.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -4.8913 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 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.9130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -5.3804 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 -2.5416 1.4674 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 -5.0832 -3.9130 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 -1.6944 -3.9130 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 -0.0000 -4.8913 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 -5.9304 -3.4239 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 -5.0832 -1.9565 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 -4.2360 -3.4239 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 -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 -2.5416 -2.4457 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8472 -1.4674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3888 -1.9565 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 -2.5416 -3.4239 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8472 -0.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8472 -5.3804 0.0000 O 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 -6.7776 -3.9130 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 -5.0832 -0.9783 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 -3.3888 -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 -3.3888 -3.9130 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 13 2 0 0 0 0 2 6 2 0 0 0 0 2 13 1 0 0 0 0 3 7 1 0 0 0 0 3 14 2 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 15 2 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 9 19 1 0 0 0 0 10 18 2 0 0 0 0 10 20 1 0 0 0 0 11 17 1 0 0 0 0 11 21 2 0 0 0 0 12 18 1 0 0 0 0 12 22 2 0 0 0 0 15 31 1 0 0 0 0 16 32 1 0 0 0 0 17 33 1 0 0 0 0 18 34 1 0 0 0 0 19 23 2 0 0 0 0 19 35 1 0 0 0 0 20 24 2 0 0 0 0 20 36 1 0 0 0 0 21 23 1 0 0 0 0 21 39 1 0 0 0 0 22 24 1 0 0 0 0 22 40 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 25 26 1 0 0 0 0 25 27 1 6 0 0 0 25 29 1 0 0 0 0 26 28 1 1 0 0 0 26 30 1 0 0 0 0 27 37 2 0 0 0 0 28 38 2 0 0 0 0 29 13 1 1 0 0 0 29 39 1 0 0 0 0 30 14 1 6 0 0 0 30 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.12
Volume:	527.089
LogP:	3.852
LogD:	2.87
LogS:	-6.219
# Rotatable Bonds:	3
TPSA:	173.98
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.216
Synthetic Accessibility Score:	4.022
Fsp3:	0.133
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.971
MDCK Permeability:	6.151519301056396e-06
Pgp-inhibitor:	0.038
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.514
20% Bioavailability (F20%):	0.554
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	98.16097259521484%
Volume Distribution (VD):	0.493
Pgp-substrate:	2.827893018722534%

ADMET: Metabolism

CYP1A2-inhibitor:	0.409
CYP1A2-substrate:	0.089
CYP2C19-inhibitor:	0.825
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.851
CYP2C9-substrate:	0.972
CYP2D6-inhibitor:	0.306
CYP2D6-substrate:	0.518
CYP3A4-inhibitor:	0.882
CYP3A4-substrate:	0.104

ADMET: Excretion

Clearance (CL):	9.829
Half-life (T1/2):	0.476

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.409
Rat Oral Acute Toxicity:	0.784
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.945
Carcinogencity:	0.11
Eye Corrosion:	0.003
Eye Irritation:	0.907
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC258474

Natural Product ID:	NPC258474
*Common Name:**	Rel-Isochamaejasmin
IUPAC Name:	(2S,3R)-3-[(2R,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	RNQBLQALVMHBKH-SQYWJIFTSA-N
Standard InCHI:	InChI=1S/C30H22O10/c31-15-5-1-13(2-6-15)29-25(27(37)23-19(35)9-17(33)11-21(23)39-29)26-28(38)24-20(36)10-18(34)12-22(24)40-30(26)14-3-7-16(32)8-4-14/h1-12,25-26,29-36H/t25-,26+,29+,30-
SMILES:	c1cc(ccc1[C@@H]1[C@@H]([C@@H]2C(=O)c3c(cc(cc3O[C@H]2c2ccc(cc2)O)O)O)C(=O)c2c(cc(cc2O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3318021
PubChem CID:	390361
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
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[15997133]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[16141313]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[16792421]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	whole plants	Panshi, Jilin Province, China	2009-JUN	PMID[21534540]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	callus	n.a.	PMID[22368856]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23611151]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[24660966]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[24931277]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25453801]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562066]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26702644]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28383891]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29148766]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184480]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	7300.0	nM	PMID[518305]

☑ 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 NPC258474 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	426
0.1-0.2	1684
0.2-0.3	3965
0.3-0.4	9656
0.4-0.5	8797
0.5-0.6	3757
0.6-0.7	5838
0.7-0.8	5190
0.8-0.85	2489
0.85-0.9	713
0.9-0.95	167
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC201227
0.9932	High Similarity	NPC309648
0.9932	High Similarity	NPC198489
0.9932	High Similarity	NPC61112
0.9866	High Similarity	NPC287789
0.9866	High Similarity	NPC271741
0.9799	High Similarity	NPC69531
0.9667	High Similarity	NPC32867
0.9603	High Similarity	NPC475184
0.96	High Similarity	NPC300668
0.96	High Similarity	NPC134171
0.9539	High Similarity	NPC295090
0.9474	High Similarity	NPC1796
0.947	High Similarity	NPC66441
0.947	High Similarity	NPC182555
0.9467	High Similarity	NPC174086
0.9419	High Similarity	NPC63438
0.9412	High Similarity	NPC51760
0.9412	High Similarity	NPC51247
0.9404	High Similarity	NPC121568
0.9351	High Similarity	NPC98023
0.9351	High Similarity	NPC226462
0.9351	High Similarity	NPC42965
0.9346	High Similarity	NPC257166
0.9329	High Similarity	NPC122894
0.9299	High Similarity	NPC224851
0.9295	High Similarity	NPC38591
0.929	High Similarity	NPC301256
0.929	High Similarity	NPC312273
0.9286	High Similarity	NPC15815
0.9286	High Similarity	NPC105584
0.9267	High Similarity	NPC3642
0.9257	High Similarity	NPC311144
0.9236	High Similarity	NPC473010
0.9231	High Similarity	NPC473012
0.9231	High Similarity	NPC473011
0.9226	High Similarity	NPC195136
0.9221	High Similarity	NPC318527
0.9221	High Similarity	NPC323627
0.9221	High Similarity	NPC324358
0.9221	High Similarity	NPC322459
0.9216	High Similarity	NPC79375
0.9216	High Similarity	NPC37253
0.9211	High Similarity	NPC39154
0.9211	High Similarity	NPC78324
0.9211	High Similarity	NPC208011
0.9211	High Similarity	NPC115601
0.9195	High Similarity	NPC299011
0.9189	High Similarity	NPC113770
0.9177	High Similarity	NPC171985
0.9177	High Similarity	NPC320741
0.9172	High Similarity	NPC473009
0.9161	High Similarity	NPC123544
0.915	High Similarity	NPC290830
0.915	High Similarity	NPC72425
0.915	High Similarity	NPC194593
0.915	High Similarity	NPC71061
0.915	High Similarity	NPC303485
0.9145	High Similarity	NPC111112
0.9145	High Similarity	NPC178484
0.9145	High Similarity	NPC316960
0.9145	High Similarity	NPC138299
0.9145	High Similarity	NPC222713
0.9145	High Similarity	NPC309512
0.9145	High Similarity	NPC78835
0.9145	High Similarity	NPC204561
0.9145	High Similarity	NPC148945
0.9145	High Similarity	NPC67322
0.9145	High Similarity	NPC317715
0.9139	High Similarity	NPC291746
0.9139	High Similarity	NPC288840
0.9139	High Similarity	NPC473016
0.9133	High Similarity	NPC308200
0.9128	High Similarity	NPC470136
0.9128	High Similarity	NPC303185
0.9128	High Similarity	NPC470135
0.9128	High Similarity	NPC184649
0.9128	High Similarity	NPC39045
0.9108	High Similarity	NPC477841
0.9108	High Similarity	NPC15374
0.9103	High Similarity	NPC121647
0.9103	High Similarity	NPC292863
0.9103	High Similarity	NPC184326
0.9097	High Similarity	NPC208258
0.9091	High Similarity	NPC265624
0.9091	High Similarity	NPC14606
0.9091	High Similarity	NPC186227
0.9091	High Similarity	NPC205026
0.9091	High Similarity	NPC52611
0.9091	High Similarity	NPC100049
0.9091	High Similarity	NPC158027
0.9091	High Similarity	NPC215203
0.9091	High Similarity	NPC150908
0.9091	High Similarity	NPC159707
0.9091	High Similarity	NPC121649
0.9091	High Similarity	NPC248739
0.9079	High Similarity	NPC29777
0.9079	High Similarity	NPC471115
0.9073	High Similarity	NPC106328
0.9073	High Similarity	NPC39195
0.9073	High Similarity	NPC145467
0.9073	High Similarity	NPC35150
0.9068	High Similarity	NPC257667
0.9068	High Similarity	NPC186847
0.9068	High Similarity	NPC472454
0.9067	High Similarity	NPC109183
0.9067	High Similarity	NPC470133
0.9067	High Similarity	NPC470134
0.9067	High Similarity	NPC473078
0.9067	High Similarity	NPC228779
0.9067	High Similarity	NPC470131
0.9067	High Similarity	NPC470132
0.9062	High Similarity	NPC53252
0.9062	High Similarity	NPC107627
0.9057	High Similarity	NPC251336
0.9057	High Similarity	NPC82330
0.9048	High Similarity	NPC316480
0.9045	High Similarity	NPC137232
0.9045	High Similarity	NPC18380
0.9038	High Similarity	NPC195167
0.9026	High Similarity	NPC326592
0.9026	High Similarity	NPC112701
0.9026	High Similarity	NPC109594
0.9013	High Similarity	NPC471114
0.9013	High Similarity	NPC132345
0.9012	High Similarity	NPC168789
0.9006	High Similarity	NPC287884
0.9006	High Similarity	NPC8704
0.9	High Similarity	NPC271288
0.8994	High Similarity	NPC477840
0.8993	High Similarity	NPC202981
0.8987	High Similarity	NPC219927
0.8986	High Similarity	NPC110228
0.8986	High Similarity	NPC76445
0.8986	High Similarity	NPC284550
0.8986	High Similarity	NPC6407
0.8986	High Similarity	NPC188243
0.8986	High Similarity	NPC129853
0.898	High Similarity	NPC118813
0.8961	High Similarity	NPC43345
0.894	High Similarity	NPC472629
0.8933	High Similarity	NPC107177
0.8933	High Similarity	NPC81697
0.8933	High Similarity	NPC223812
0.8933	High Similarity	NPC278249
0.8933	High Similarity	NPC85162
0.8933	High Similarity	NPC125894
0.8933	High Similarity	NPC77794
0.8931	High Similarity	NPC290160
0.8924	High Similarity	NPC97812
0.8924	High Similarity	NPC114652
0.8924	High Similarity	NPC175513
0.8919	High Similarity	NPC225153
0.8919	High Similarity	NPC310135
0.8919	High Similarity	NPC20709
0.8919	High Similarity	NPC140890
0.8919	High Similarity	NPC329203
0.8919	High Similarity	NPC222342
0.8919	High Similarity	NPC150648
0.8919	High Similarity	NPC265871
0.8919	High Similarity	NPC274784
0.8919	High Similarity	NPC261234
0.8917	High Similarity	NPC308265
0.8912	High Similarity	NPC296490
0.8912	High Similarity	NPC79943
0.8912	High Similarity	NPC12296
0.8912	High Similarity	NPC13768
0.8912	High Similarity	NPC32441
0.8912	High Similarity	NPC295261
0.8912	High Similarity	NPC243083
0.8912	High Similarity	NPC287246
0.8912	High Similarity	NPC107586
0.891	High Similarity	NPC54830
0.891	High Similarity	NPC56049
0.8903	High Similarity	NPC203080
0.8903	High Similarity	NPC244250
0.8903	High Similarity	NPC20907
0.8903	High Similarity	NPC324447
0.8896	High Similarity	NPC312549
0.8896	High Similarity	NPC476553
0.8896	High Similarity	NPC477897
0.8896	High Similarity	NPC209142
0.8896	High Similarity	NPC476552
0.8896	High Similarity	NPC289774
0.8896	High Similarity	NPC209846
0.8896	High Similarity	NPC328740
0.8896	High Similarity	NPC476551
0.8882	High Similarity	NPC296998
0.8882	High Similarity	NPC475348
0.8882	High Similarity	NPC10990
0.8882	High Similarity	NPC473077
0.8882	High Similarity	NPC300988
0.8882	High Similarity	NPC261271
0.8875	High Similarity	NPC474591
0.8874	High Similarity	NPC124780
0.8874	High Similarity	NPC470890
0.8874	High Similarity	NPC235217
0.8874	High Similarity	NPC473015
0.8874	High Similarity	NPC473014
0.8874	High Similarity	NPC131568

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 NPC258474 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	394
0.1-0.2	937
0.2-0.3	1609
0.3-0.4	2655
0.4-0.5	1875
0.5-0.6	1111
0.6-0.7	380
0.7-0.8	139
0.8-0.85	35
0.85-0.9	12
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD8443	Clinical (unspecified phase)
0.9045	High Similarity	NPD6959	Discontinued
0.8912	High Similarity	NPD1552	Clinical (unspecified phase)
0.8912	High Similarity	NPD1550	Clinical (unspecified phase)
0.8851	High Similarity	NPD1549	Phase 2
0.8758	High Similarity	NPD6167	Clinical (unspecified phase)
0.8758	High Similarity	NPD6168	Clinical (unspecified phase)
0.8758	High Similarity	NPD6166	Phase 2
0.8758	High Similarity	NPD7852	Clinical (unspecified phase)
0.871	High Similarity	NPD4380	Phase 2
0.8654	High Similarity	NPD7411	Suspended
0.8627	High Similarity	NPD7410	Clinical (unspecified phase)
0.8627	High Similarity	NPD4378	Clinical (unspecified phase)
0.8616	High Similarity	NPD4381	Clinical (unspecified phase)
0.8544	High Similarity	NPD2393	Clinical (unspecified phase)
0.8523	High Similarity	NPD1510	Phase 2
0.85	High Similarity	NPD3749	Approved
0.8481	Intermediate Similarity	NPD1934	Approved
0.8467	Intermediate Similarity	NPD2796	Approved
0.8438	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD7768	Phase 2
0.8385	Intermediate Similarity	NPD7075	Discontinued
0.8383	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7074	Phase 3
0.8313	Intermediate Similarity	NPD7819	Suspended
0.8282	Intermediate Similarity	NPD5494	Approved
0.8263	Intermediate Similarity	NPD7054	Approved
0.8255	Intermediate Similarity	NPD1240	Approved
0.8214	Intermediate Similarity	NPD7472	Approved
0.8205	Intermediate Similarity	NPD1511	Approved
0.8199	Intermediate Similarity	NPD2801	Approved
0.8199	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD6797	Phase 2
0.8146	Intermediate Similarity	NPD1607	Approved
0.8144	Intermediate Similarity	NPD7473	Discontinued
0.8129	Intermediate Similarity	NPD3750	Approved
0.8118	Intermediate Similarity	NPD7251	Discontinued
0.8108	Intermediate Similarity	NPD4908	Phase 1
0.8101	Intermediate Similarity	NPD1512	Approved
0.8095	Intermediate Similarity	NPD3818	Discontinued
0.8072	Intermediate Similarity	NPD6232	Discontinued
0.807	Intermediate Similarity	NPD7808	Phase 3
0.8025	Intermediate Similarity	NPD6801	Discontinued
0.8023	Intermediate Similarity	NPD8312	Approved
0.8023	Intermediate Similarity	NPD8313	Approved
0.8	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD3882	Suspended
0.7975	Intermediate Similarity	NPD6799	Approved
0.7975	Intermediate Similarity	NPD7390	Discontinued
0.7965	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD2800	Approved
0.7937	Intermediate Similarity	NPD5403	Approved
0.7935	Intermediate Similarity	NPD2344	Approved
0.7927	Intermediate Similarity	NPD3817	Phase 2
0.7927	Intermediate Similarity	NPD5402	Approved
0.7901	Intermediate Similarity	NPD6599	Discontinued
0.7885	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1551	Phase 2
0.7836	Intermediate Similarity	NPD5844	Phase 1
0.7812	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5401	Approved
0.7806	Intermediate Similarity	NPD3748	Approved
0.7803	Intermediate Similarity	NPD6559	Discontinued
0.7763	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD8455	Phase 2
0.7758	Intermediate Similarity	NPD1465	Phase 2
0.7755	Intermediate Similarity	NPD1610	Phase 2
0.7746	Intermediate Similarity	NPD5953	Discontinued
0.7736	Intermediate Similarity	NPD2309	Approved
0.773	Intermediate Similarity	NPD3226	Approved
0.7709	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2533	Approved
0.7702	Intermediate Similarity	NPD2534	Approved
0.7702	Intermediate Similarity	NPD2532	Approved
0.7692	Intermediate Similarity	NPD2799	Discontinued
0.7677	Intermediate Similarity	NPD6651	Approved
0.7674	Intermediate Similarity	NPD3751	Discontinued
0.7673	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3787	Discontinued
0.7643	Intermediate Similarity	NPD6099	Approved
0.7643	Intermediate Similarity	NPD6100	Approved
0.7635	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD4360	Phase 2
0.7624	Intermediate Similarity	NPD4363	Phase 3
0.7607	Intermediate Similarity	NPD920	Approved
0.7602	Intermediate Similarity	NPD3926	Phase 2
0.7593	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4628	Phase 3
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7532	Intermediate Similarity	NPD2935	Discontinued
0.7529	Intermediate Similarity	NPD7286	Phase 2
0.7515	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4287	Approved
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD8151	Discontinued
0.7469	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD943	Approved
0.7434	Intermediate Similarity	NPD1203	Approved
0.7425	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6782	Approved
0.7419	Intermediate Similarity	NPD6778	Approved
0.7419	Intermediate Similarity	NPD6776	Approved
0.7419	Intermediate Similarity	NPD6777	Approved
0.7419	Intermediate Similarity	NPD6779	Approved
0.7419	Intermediate Similarity	NPD3268	Approved
0.7419	Intermediate Similarity	NPD6780	Approved
0.7419	Intermediate Similarity	NPD6781	Approved
0.741	Intermediate Similarity	NPD7458	Discontinued
0.7403	Intermediate Similarity	NPD6832	Phase 2
0.7394	Intermediate Similarity	NPD7698	Approved
0.7394	Intermediate Similarity	NPD7696	Phase 3
0.7394	Intermediate Similarity	NPD7697	Approved
0.7391	Intermediate Similarity	NPD1243	Approved
0.7386	Intermediate Similarity	NPD2798	Approved
0.7375	Intermediate Similarity	NPD2346	Discontinued
0.7365	Intermediate Similarity	NPD1548	Phase 1
0.7358	Intermediate Similarity	NPD7033	Discontinued
0.7354	Intermediate Similarity	NPD7870	Phase 2
0.7354	Intermediate Similarity	NPD7871	Phase 2
0.7351	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7003	Approved
0.7341	Intermediate Similarity	NPD7229	Phase 3
0.7338	Intermediate Similarity	NPD2861	Phase 2
0.7325	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1613	Approved
0.732	Intermediate Similarity	NPD2797	Approved
0.7312	Intermediate Similarity	NPD5404	Approved
0.7312	Intermediate Similarity	NPD5406	Approved
0.7312	Intermediate Similarity	NPD5405	Approved
0.7312	Intermediate Similarity	NPD5408	Approved
0.7308	Intermediate Similarity	NPD3764	Approved
0.7302	Intermediate Similarity	NPD7435	Discontinued
0.7296	Intermediate Similarity	NPD7097	Phase 1
0.7289	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7199	Phase 2
0.7278	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD7228	Approved
0.7273	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5711	Approved
0.7241	Intermediate Similarity	NPD5710	Approved
0.724	Intermediate Similarity	NPD7701	Phase 2
0.7216	Intermediate Similarity	NPD7783	Phase 2
0.7216	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7213	Phase 3
0.7212	Intermediate Similarity	NPD7212	Phase 2
0.7208	Intermediate Similarity	NPD1470	Approved
0.7204	Intermediate Similarity	NPD4361	Phase 2
0.7204	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8150	Discontinued
0.7198	Intermediate Similarity	NPD8434	Phase 2
0.7197	Intermediate Similarity	NPD6798	Discontinued
0.7193	Intermediate Similarity	NPD2296	Approved
0.7193	Intermediate Similarity	NPD4288	Approved
0.7184	Intermediate Similarity	NPD1247	Approved
0.7179	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6844	Discontinued
0.7176	Intermediate Similarity	NPD7577	Discontinued
0.7176	Intermediate Similarity	NPD37	Approved
0.7169	Intermediate Similarity	NPD7447	Phase 1
0.7168	Intermediate Similarity	NPD6234	Discontinued
0.7151	Intermediate Similarity	NPD4965	Approved
0.7151	Intermediate Similarity	NPD6534	Approved
0.7151	Intermediate Similarity	NPD6535	Approved
0.7151	Intermediate Similarity	NPD4967	Phase 2
0.7151	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD3225	Approved
0.7143	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5760	Phase 2
0.7135	Intermediate Similarity	NPD5761	Phase 2
0.7128	Intermediate Similarity	NPD7700	Phase 2
0.7128	Intermediate Similarity	NPD7699	Phase 2
0.7128	Intermediate Similarity	NPD7801	Approved
0.7126	Intermediate Similarity	NPD6273	Approved
0.7124	Intermediate Similarity	NPD9717	Approved
0.7124	Intermediate Similarity	NPD1608	Approved
0.7115	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7584	Approved
0.7097	Intermediate Similarity	NPD3266	Approved
0.7097	Intermediate Similarity	NPD3267	Approved
0.7083	Intermediate Similarity	NPD8320	Phase 1
0.7083	Intermediate Similarity	NPD8319	Approved
0.7079	Intermediate Similarity	NPD7177	Discontinued
0.7079	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4749	Approved
0.7077	Intermediate Similarity	NPD7874	Approved
0.7077	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6280	Approved
0.7076	Intermediate Similarity	NPD6279	Approved
0.7073	Intermediate Similarity	NPD2654	Approved
0.7069	Intermediate Similarity	NPD919	Approved
0.7068	Intermediate Similarity	NPD6823	Phase 2

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