NPASS Compound

Structure

CID41844 OpenBabel06191715372D 24 26 0 0 1 0 0 0 0 0999 V2000 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 6 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 9 1 0 0 0 0 5 16 1 0 0 0 0 6 14 2 0 0 0 0 7 11 2 0 0 0 0 7 22 1 0 0 0 0 8 5 1 6 0 0 0 8 10 1 0 0 0 0 8 23 1 0 0 0 0 9 17 2 0 0 0 0 9 24 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 1 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 6 0 0 0 13 15 1 0 0 0 0 13 21 1 1 0 0 0 14 24 1 0 0 0 0 15 22 1 6 0 0 0 15 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.08
Volume:	308.257
LogP:	-0.608
LogD:	-0.536
LogS:	-1.706
# Rotatable Bonds:	3
TPSA:	149.82
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.429
Synthetic Accessibility Score:	3.819
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.033
MDCK Permeability:	2.8000511520076543e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.206
Human Intestinal Absorption (HIA):	0.413
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.149
Plasma Protein Binding (PPB):	72.09223175048828%
Volume Distribution (VD):	0.768
Pgp-substrate:	25.763957977294922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.172
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.2
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.026

ADMET: Excretion

Clearance (CL):	2.784
Half-life (T1/2):	0.831

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.367
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.362
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.281
Carcinogencity:	0.731
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC41844

Natural Product ID:	NPC41844
*Common Name:**	8-Hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxychromen-2-One
IUPAC Name:	8-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
Synonyms:
Standard InCHIKey:	HOIXTKAYCMNVMY-PVOAASPHSA-N
Standard InCHI:	InChI=1S/C15H16O9/c16-5-8-10(18)12(20)13(21)15(23-8)22-7-3-1-6-2-4-9(17)24-14(6)11(7)19/h1-4,8,10,12-13,15-16,18-21H,5H2/t8-,10-,12+,13-,15-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc3c(c2O)oc(=O)cc3)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1879316
PubChem CID:	439499
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0001743] Coumarin glycosides

*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
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	stem bark	Kunming, Yunnan Province, China	n.a.	PMID[18986199]
NPO19803	Oxytropis ochrocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22494026]
NPO14508	Aconitum heterophyllum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[24156713]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32997496]
NPO16297	Gentiana arisanensis	Species	Gentianaceae	Eukaryota	Whole Plant	Yu Shieh, Chiayi Hsieh, Taiwan	1994-APR	PMID[9287421]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12948	Solanum dulcamara	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14508	Aconitum heterophyllum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18816	Lindera glauca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12444	Astragalus sinicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14508	Aconitum heterophyllum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12948	Solanum dulcamara	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18816	Lindera glauca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23754	Solanum aculeatissimum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18393	Eugenia sandwicensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12444	Astragalus sinicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16416	Serratula strangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12948	Solanum dulcamara	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12444	Astragalus sinicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15287	Vernonia megapotamica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16416	Serratula strangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16297	Gentiana arisanensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18247	Globicephala melas	Species	Delphinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10882	Acer caudatifolium	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19479	Trametes feei	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12444	Astragalus sinicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13505	Grateloupia livida	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14015	Salacia cordata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17558	Cynoglossum formosanum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12948	Solanum dulcamara	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10705	Marshallia graminifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23754	Solanum aculeatissimum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12376	Baccharis macraei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7037	Rumohra adiantiformis	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18393	Eugenia sandwicensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19803	Oxytropis ochrocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17135	Mikania goyazensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15721	Derris reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16918	Ballota lanata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18413	Eucalyptus ovata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10211	Pajanelia multijuga	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21329	Ilyonectria destructans	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18816	Lindera glauca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14508	Aconitum heterophyllum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19406	Chrysanthemum leptophyllum	Species	Asteraceae	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
Potency	5

Activity Type	# Activity
Individual Protein	3
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[522232]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[522233]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	130.0	nM	PMID[522233]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[522233]
NPT2	Others	Unspecified		Potency	n.a.	15848.9	nM	PMID[522233]

☑ 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 NPC41844 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	420
0.1-0.2	1899
0.2-0.3	4734
0.3-0.4	10000
0.4-0.5	7893
0.5-0.6	4174
0.6-0.7	5215
0.7-0.8	5513
0.8-0.85	1933
0.85-0.9	724
0.9-0.95	187
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9858	High Similarity	NPC313334
0.9858	High Similarity	NPC212670
0.9858	High Similarity	NPC206264
0.972	High Similarity	NPC213197
0.9577	High Similarity	NPC52740
0.951	High Similarity	NPC96294
0.9452	High Similarity	NPC150442
0.9384	High Similarity	NPC176186
0.9384	High Similarity	NPC169404
0.9384	High Similarity	NPC53587
0.9379	High Similarity	NPC114740
0.9375	High Similarity	NPC93924
0.9371	High Similarity	NPC199928
0.9366	High Similarity	NPC292443
0.9366	High Similarity	NPC232228
0.931	High Similarity	NPC106138
0.9281	High Similarity	NPC103409
0.9281	High Similarity	NPC186418
0.9252	High Similarity	NPC215060
0.9252	High Similarity	NPC476352
0.9241	High Similarity	NPC187398
0.9241	High Similarity	NPC478237
0.9241	High Similarity	NPC476348
0.922	High Similarity	NPC202700
0.9172	High Similarity	NPC476347
0.9161	High Similarity	NPC478239
0.9155	High Similarity	NPC186406
0.9149	High Similarity	NPC100389
0.9122	High Similarity	NPC470264
0.9116	High Similarity	NPC120426
0.9116	High Similarity	NPC21184
0.9116	High Similarity	NPC294522
0.9116	High Similarity	NPC205727
0.9097	High Similarity	NPC297342
0.9091	High Similarity	NPC475084
0.9091	High Similarity	NPC157816
0.9048	High Similarity	NPC176903
0.9048	High Similarity	NPC30688
0.9034	High Similarity	NPC476450
0.9028	High Similarity	NPC252169
0.9021	High Similarity	NPC476442
0.9021	High Similarity	NPC215512
0.9014	High Similarity	NPC13067
0.9007	High Similarity	NPC284810
0.9007	High Similarity	NPC37468
0.9007	High Similarity	NPC157554
0.9	High Similarity	NPC92830
0.8966	High Similarity	NPC471763
0.8958	High Similarity	NPC145319
0.8958	High Similarity	NPC140502
0.8951	High Similarity	NPC210478
0.8944	High Similarity	NPC20511
0.8944	High Similarity	NPC59324
0.8944	High Similarity	NPC52086
0.8944	High Similarity	NPC95162
0.8944	High Similarity	NPC65530
0.8944	High Similarity	NPC76336
0.8944	High Similarity	NPC148835
0.8944	High Similarity	NPC139548
0.8936	High Similarity	NPC185778
0.8921	High Similarity	NPC73738
0.8921	High Similarity	NPC166168
0.8919	High Similarity	NPC283839
0.8919	High Similarity	NPC90896
0.8912	High Similarity	NPC15577
0.8904	High Similarity	NPC226722
0.8904	High Similarity	NPC85624
0.8904	High Similarity	NPC476869
0.8904	High Similarity	NPC476864
0.8904	High Similarity	NPC475096
0.8904	High Similarity	NPC476868
0.8904	High Similarity	NPC476866
0.8889	High Similarity	NPC300611
0.8889	High Similarity	NPC469661
0.8881	High Similarity	NPC226005
0.8881	High Similarity	NPC164148
0.8881	High Similarity	NPC212770
0.8881	High Similarity	NPC98777
0.8881	High Similarity	NPC43500
0.8873	High Similarity	NPC126682
0.8873	High Similarity	NPC242028
0.8873	High Similarity	NPC166180
0.8873	High Similarity	NPC203230
0.8873	High Similarity	NPC82271
0.8867	High Similarity	NPC163598
0.8867	High Similarity	NPC120774
0.8867	High Similarity	NPC264875
0.8865	High Similarity	NPC87696
0.8857	High Similarity	NPC470270
0.8857	High Similarity	NPC299144
0.8851	High Similarity	NPC169510
0.8844	High Similarity	NPC268515
0.8844	High Similarity	NPC476865
0.8844	High Similarity	NPC190714
0.8844	High Similarity	NPC40222
0.8844	High Similarity	NPC125755
0.8844	High Similarity	NPC99515
0.8836	High Similarity	NPC168579
0.8836	High Similarity	NPC469313
0.8836	High Similarity	NPC476867
0.8836	High Similarity	NPC138227
0.8836	High Similarity	NPC76176
0.8828	High Similarity	NPC469559
0.8828	High Similarity	NPC189115
0.8811	High Similarity	NPC124149
0.8808	High Similarity	NPC105827
0.8808	High Similarity	NPC310661
0.8794	High Similarity	NPC132895
0.8794	High Similarity	NPC49074
0.8784	High Similarity	NPC227902
0.8784	High Similarity	NPC87950
0.8784	High Similarity	NPC471764
0.8784	High Similarity	NPC296377
0.8776	High Similarity	NPC252292
0.8776	High Similarity	NPC277867
0.8776	High Similarity	NPC34587
0.8776	High Similarity	NPC100998
0.8776	High Similarity	NPC161700
0.8776	High Similarity	NPC476382
0.8776	High Similarity	NPC34927
0.8767	High Similarity	NPC138212
0.8767	High Similarity	NPC37793
0.8766	High Similarity	NPC160780
0.8766	High Similarity	NPC289811
0.8742	High Similarity	NPC472612
0.8742	High Similarity	NPC289967
0.8742	High Similarity	NPC472611
0.8741	High Similarity	NPC471664
0.8741	High Similarity	NPC164857
0.8741	High Similarity	NPC471665
0.8741	High Similarity	NPC104167
0.8733	High Similarity	NPC476871
0.8732	High Similarity	NPC251981
0.8732	High Similarity	NPC13745
0.8732	High Similarity	NPC309953
0.8732	High Similarity	NPC48863
0.8732	High Similarity	NPC107478
0.8725	High Similarity	NPC175976
0.8723	High Similarity	NPC137949
0.8723	High Similarity	NPC162093
0.8716	High Similarity	NPC205361
0.871	High Similarity	NPC239966
0.871	High Similarity	NPC203020
0.8707	High Similarity	NPC473045
0.8707	High Similarity	NPC25292
0.8707	High Similarity	NPC110063
0.8705	High Similarity	NPC146540
0.8705	High Similarity	NPC232880
0.8701	High Similarity	NPC1913
0.8699	High Similarity	NPC278469
0.8699	High Similarity	NPC193722
0.8684	High Similarity	NPC246893
0.8681	High Similarity	NPC20796
0.8681	High Similarity	NPC126206
0.8671	High Similarity	NPC55040
0.8671	High Similarity	NPC476870
0.8671	High Similarity	NPC470236
0.8662	High Similarity	NPC26673
0.8662	High Similarity	NPC121290
0.8662	High Similarity	NPC215833
0.8662	High Similarity	NPC69513
0.8658	High Similarity	NPC15538
0.8658	High Similarity	NPC473480
0.8658	High Similarity	NPC232992
0.8654	High Similarity	NPC25389
0.8654	High Similarity	NPC311803
0.8654	High Similarity	NPC472859
0.8649	High Similarity	NPC287615
0.8649	High Similarity	NPC83743
0.8649	High Similarity	NPC262182
0.8649	High Similarity	NPC216819
0.8645	High Similarity	NPC287872
0.8645	High Similarity	NPC74319
0.8643	High Similarity	NPC477294
0.8643	High Similarity	NPC229784
0.8643	High Similarity	NPC477293
0.8643	High Similarity	NPC48315
0.8643	High Similarity	NPC166040
0.8639	High Similarity	NPC236419
0.8639	High Similarity	NPC7439
0.8639	High Similarity	NPC34245
0.8639	High Similarity	NPC256555
0.8639	High Similarity	NPC110067
0.8639	High Similarity	NPC91492
0.8639	High Similarity	NPC473044
0.8634	High Similarity	NPC163165
0.8633	High Similarity	NPC476873
0.863	High Similarity	NPC224876
0.863	High Similarity	NPC83375
0.8627	High Similarity	NPC8712
0.8618	High Similarity	NPC302610
0.8616	High Similarity	NPC116745
0.8609	High Similarity	NPC100818
0.8601	High Similarity	NPC7163
0.8601	High Similarity	NPC886
0.8601	High Similarity	NPC34293
0.8601	High Similarity	NPC287597
0.8601	High Similarity	NPC111635
0.86	High Similarity	NPC280945
0.8599	High Similarity	NPC285108

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 NPC41844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	969
0.2-0.3	2113
0.3-0.4	2625
0.4-0.5	1749
0.5-0.6	881
0.6-0.7	277
0.7-0.8	117
0.8-0.85	22
0.85-0.9	12
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9858	High Similarity	NPD1653	Approved
0.8462	Intermediate Similarity	NPD1613	Approved
0.8462	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD3818	Discontinued
0.8367	Intermediate Similarity	NPD7266	Discontinued
0.8354	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7054	Approved
0.8282	Intermediate Similarity	NPD7472	Approved
0.8201	Intermediate Similarity	NPD1091	Approved
0.8182	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7074	Phase 3
0.8165	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1652	Phase 2
0.8121	Intermediate Similarity	NPD6797	Phase 2
0.8113	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD7251	Discontinued
0.8024	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD3027	Phase 3
0.7943	Intermediate Similarity	NPD422	Phase 1
0.7862	Intermediate Similarity	NPD1934	Approved
0.784	Intermediate Similarity	NPD6234	Discontinued
0.7831	Intermediate Similarity	NPD7228	Approved
0.7812	Intermediate Similarity	NPD1465	Phase 2
0.7785	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD5124	Phase 1
0.7764	Intermediate Similarity	NPD3817	Phase 2
0.7751	Intermediate Similarity	NPD6559	Discontinued
0.775	Intermediate Similarity	NPD37	Approved
0.7744	Intermediate Similarity	NPD7199	Phase 2
0.7716	Intermediate Similarity	NPD4966	Approved
0.7716	Intermediate Similarity	NPD4967	Phase 2
0.7716	Intermediate Similarity	NPD4965	Approved
0.7711	Intermediate Similarity	NPD6166	Phase 2
0.7711	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2801	Approved
0.7702	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1511	Approved
0.7692	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5844	Phase 1
0.7647	Intermediate Similarity	NPD7685	Pre-registration
0.7595	Intermediate Similarity	NPD1512	Approved
0.7574	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6190	Approved
0.755	Intermediate Similarity	NPD230	Phase 1
0.7548	Intermediate Similarity	NPD6674	Discontinued
0.7546	Intermediate Similarity	NPD5402	Approved
0.7545	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1548	Phase 1
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD3882	Suspended
0.7455	Intermediate Similarity	NPD7075	Discontinued
0.7448	Intermediate Similarity	NPD1610	Phase 2
0.7438	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5403	Approved
0.7434	Intermediate Similarity	NPD447	Suspended
0.7399	Intermediate Similarity	NPD7549	Discontinued
0.7386	Intermediate Similarity	NPD6842	Approved
0.7386	Intermediate Similarity	NPD6841	Approved
0.7386	Intermediate Similarity	NPD6843	Phase 3
0.7378	Intermediate Similarity	NPD8455	Phase 2
0.7361	Intermediate Similarity	NPD1357	Approved
0.7358	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7240	Approved
0.7333	Intermediate Similarity	NPD4908	Phase 1
0.7317	Intermediate Similarity	NPD6801	Discontinued
0.7312	Intermediate Similarity	NPD5401	Approved
0.7278	Intermediate Similarity	NPD3750	Approved
0.7278	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3018	Phase 2
0.7261	Intermediate Similarity	NPD1549	Phase 2
0.7244	Intermediate Similarity	NPD1551	Phase 2
0.7237	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3705	Approved
0.7209	Intermediate Similarity	NPD3751	Discontinued
0.7208	Intermediate Similarity	NPD1933	Approved
0.7197	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3225	Approved
0.7176	Intermediate Similarity	NPD6232	Discontinued
0.7169	Intermediate Similarity	NPD7819	Suspended
0.7163	Intermediate Similarity	NPD228	Approved
0.7159	Intermediate Similarity	NPD8313	Approved
0.7159	Intermediate Similarity	NPD8312	Approved
0.7152	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2861	Phase 2
0.7143	Intermediate Similarity	NPD6799	Approved
0.7143	Intermediate Similarity	NPD3496	Discontinued
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7124	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD8127	Discontinued
0.7114	Intermediate Similarity	NPD4749	Approved
0.7114	Intermediate Similarity	NPD2982	Phase 2
0.7114	Intermediate Similarity	NPD2983	Phase 2
0.7105	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD919	Approved
0.7097	Intermediate Similarity	NPD4340	Discontinued
0.7076	Intermediate Similarity	NPD3787	Discontinued
0.7073	Intermediate Similarity	NPD3686	Approved
0.7073	Intermediate Similarity	NPD3687	Approved
0.707	Intermediate Similarity	NPD1510	Phase 2
0.7063	Intermediate Similarity	NPD4628	Phase 3
0.7059	Intermediate Similarity	NPD5494	Approved
0.7056	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7473	Discontinued
0.7048	Intermediate Similarity	NPD7411	Suspended
0.7047	Intermediate Similarity	NPD2981	Phase 2
0.7027	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1296	Phase 2
0.7006	Intermediate Similarity	NPD7097	Phase 1
0.7	Intermediate Similarity	NPD1358	Approved
0.7	Intermediate Similarity	NPD290	Approved
0.6994	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD9697	Approved
0.6978	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7680	Approved
0.6962	Remote Similarity	NPD3748	Approved
0.6959	Remote Similarity	NPD1778	Approved
0.6948	Remote Similarity	NPD4625	Phase 3
0.6941	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2424	Discontinued
0.6933	Remote Similarity	NPD4357	Discontinued
0.6933	Remote Similarity	NPD9269	Phase 2
0.6928	Remote Similarity	NPD9494	Approved
0.6923	Remote Similarity	NPD5353	Approved
0.6918	Remote Similarity	NPD2796	Approved
0.6911	Remote Similarity	NPD7585	Approved
0.6908	Remote Similarity	NPD1203	Approved
0.6908	Remote Similarity	NPD2797	Approved
0.6903	Remote Similarity	NPD6798	Discontinued
0.6899	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6599	Discontinued
0.6882	Remote Similarity	NPD7768	Phase 2
0.6875	Remote Similarity	NPD5762	Approved
0.6875	Remote Similarity	NPD5763	Approved
0.6871	Remote Similarity	NPD5536	Phase 2
0.6871	Remote Similarity	NPD5058	Phase 3
0.6859	Remote Similarity	NPD6233	Phase 2
0.6859	Remote Similarity	NPD7583	Approved
0.6855	Remote Similarity	NPD7033	Discontinued
0.6848	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6653	Approved
0.6833	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD9717	Approved
0.6815	Remote Similarity	NPD1558	Phase 1
0.6813	Remote Similarity	NPD2935	Discontinued
0.68	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3268	Approved
0.679	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4675	Approved
0.6786	Remote Similarity	NPD4678	Approved
0.6772	Remote Similarity	NPD6355	Discontinued
0.677	Remote Similarity	NPD3540	Phase 1
0.677	Remote Similarity	NPD1375	Discontinued
0.6765	Remote Similarity	NPD2978	Approved
0.6765	Remote Similarity	NPD2977	Approved
0.676	Remote Similarity	NPD7039	Approved
0.676	Remote Similarity	NPD7038	Approved
0.6759	Remote Similarity	NPD7843	Approved
0.6748	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4110	Phase 3
0.6744	Remote Similarity	NPD3749	Approved
0.6735	Remote Similarity	NPD7157	Approved
0.6735	Remote Similarity	NPD6671	Approved
0.6733	Remote Similarity	NPD4626	Approved
0.6732	Remote Similarity	NPD8651	Approved
0.6731	Remote Similarity	NPD7095	Approved
0.6727	Remote Similarity	NPD7212	Phase 2
0.6727	Remote Similarity	NPD7213	Phase 3
0.6727	Remote Similarity	NPD1774	Approved
0.6726	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1247	Approved
0.6724	Remote Similarity	NPD6959	Discontinued
0.6713	Remote Similarity	NPD2684	Approved
0.6709	Remote Similarity	NPD1240	Approved
0.6709	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4140	Approved
0.6709	Remote Similarity	NPD943	Approved
0.6709	Remote Similarity	NPD3620	Phase 2
0.6708	Remote Similarity	NPD6100	Approved
0.6708	Remote Similarity	NPD6099	Approved
0.6708	Remote Similarity	NPD3539	Phase 1
0.6707	Remote Similarity	NPD2219	Phase 1
0.6707	Remote Similarity	NPD920	Approved
0.6701	Remote Similarity	NPD8151	Discontinued
0.669	Remote Similarity	NPD3134	Approved
0.669	Remote Similarity	NPD969	Suspended
0.6688	Remote Similarity	NPD1048	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data