NPASS Compound

Structure

CID313334 OpenBabel06191716122D 24 26 0 0 1 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 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 -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 -3.4641 -2.0000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 3 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 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 O 0 0 0 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 0.0000 -3.0000 0.0000 O 0 0 0 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 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 2 2 0 0 0 0 1 6 1 0 0 0 0 2 11 1 0 0 0 0 3 6 2 0 0 0 0 3 9 1 0 0 0 0 4 7 1 0 0 0 0 4 8 2 0 0 0 0 5 10 1 0 0 0 0 5 16 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 7 17 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 18 2 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 15 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.08
Volume:	308.257
LogP:	-1.068
LogD:	-0.055
LogS:	-1.985
# 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:	3.732
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:	-5.95
MDCK Permeability:	0.0001860593183664605
Pgp-inhibitor:	0.001
Pgp-substrate:	0.491
Human Intestinal Absorption (HIA):	0.829
20% Bioavailability (F20%):	0.534
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.765
Plasma Protein Binding (PPB):	56.10059356689453%
Volume Distribution (VD):	0.626
Pgp-substrate:	45.491390228271484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.315
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.25
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.027

ADMET: Excretion

Clearance (CL):	4.015
Half-life (T1/2):	0.592

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.813
AMES Toxicity:	0.293
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.05
Carcinogencity:	0.738
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC313334

Natural Product ID:	NPC313334
*Common Name:**	7-Hydroxy-6-[3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxychromen-2-One
IUPAC Name:	7-hydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
Synonyms:
Standard InCHIKey:	XHCADAYNFIFUHF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2
SMILES:	OCC1OC(Oc2cc3ccc(=O)oc3cc2O)C(C(C1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL359043
PubChem CID:	5351506
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
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruit	n.a.	n.a.	DOI[10.1016/S0963-9969(99)00095-2]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542364]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21381697]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30817151]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruit	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruits	n.a.		Database[FooDB]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruits	n.a.		Database[Phenol-Explorer]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.		Database[Phenol-Explorer]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28236	Cortex fraxini	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO12407	Herba cichorii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO21321	Semen euphorbiae pulveratum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9518	Gardenia jasminoides	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
Potency	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	13335.9	nM	PMID[528321]

☑ 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 NPC313334 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	423
0.1-0.2	1942
0.2-0.3	4799
0.3-0.4	10075
0.4-0.5	7833
0.5-0.6	4121
0.6-0.7	5248
0.7-0.8	5322
0.8-0.85	1976
0.85-0.9	770
0.9-0.95	182
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC212670
1.0	High Similarity	NPC206264
0.986	High Similarity	NPC213197
0.9858	High Similarity	NPC41844
0.965	High Similarity	NPC96294
0.9517	High Similarity	NPC114740
0.9444	High Similarity	NPC52740
0.9379	High Similarity	NPC478237
0.9324	High Similarity	NPC150442
0.9257	High Similarity	NPC176186
0.9257	High Similarity	NPC169404
0.9257	High Similarity	NPC53587
0.9252	High Similarity	NPC294522
0.9252	High Similarity	NPC120426
0.9252	High Similarity	NPC21184
0.9252	High Similarity	NPC205727
0.9247	High Similarity	NPC93924
0.9241	High Similarity	NPC199928
0.9236	High Similarity	NPC232228
0.9236	High Similarity	NPC292443
0.9184	High Similarity	NPC106138
0.9184	High Similarity	NPC30688
0.9184	High Similarity	NPC176903
0.9172	High Similarity	NPC476450
0.9167	High Similarity	NPC252169
0.9155	High Similarity	NPC13067
0.9149	High Similarity	NPC103409
0.9149	High Similarity	NPC186418
0.9139	High Similarity	NPC284810
0.9128	High Similarity	NPC476352
0.9128	High Similarity	NPC215060
0.9116	High Similarity	NPC476348
0.9116	High Similarity	NPC187398
0.9097	High Similarity	NPC145319
0.9091	High Similarity	NPC202700
0.9085	High Similarity	NPC52086
0.9085	High Similarity	NPC139548
0.9085	High Similarity	NPC148835
0.9085	High Similarity	NPC20511
0.9085	High Similarity	NPC95162
0.9085	High Similarity	NPC76336
0.9048	High Similarity	NPC476347
0.9048	High Similarity	NPC15577
0.9034	High Similarity	NPC478239
0.9028	High Similarity	NPC300611
0.9028	High Similarity	NPC186406
0.9021	High Similarity	NPC100389
0.9021	High Similarity	NPC43500
0.9021	High Similarity	NPC164148
0.9014	High Similarity	NPC82271
0.9014	High Similarity	NPC126682
0.9	High Similarity	NPC470264
0.9	High Similarity	NPC264875
0.9	High Similarity	NPC120774
0.9	High Similarity	NPC163598
0.8973	High Similarity	NPC297342
0.8966	High Similarity	NPC475084
0.8966	High Similarity	NPC157816
0.8919	High Similarity	NPC227902
0.8904	High Similarity	NPC138212
0.8897	High Similarity	NPC476442
0.8897	High Similarity	NPC215512
0.8881	High Similarity	NPC37468
0.8881	High Similarity	NPC104167
0.8881	High Similarity	NPC157554
0.8873	High Similarity	NPC309953
0.8873	High Similarity	NPC92830
0.8865	High Similarity	NPC137949
0.8859	High Similarity	NPC175976
0.8851	High Similarity	NPC205361
0.8844	High Similarity	NPC471763
0.8836	High Similarity	NPC140502
0.8828	High Similarity	NPC210478
0.8819	High Similarity	NPC65530
0.8819	High Similarity	NPC20796
0.8819	High Similarity	NPC59324
0.8811	High Similarity	NPC185778
0.8803	High Similarity	NPC26673
0.88	High Similarity	NPC283839
0.88	High Similarity	NPC90896
0.8794	High Similarity	NPC73738
0.8794	High Similarity	NPC166168
0.8784	High Similarity	NPC476864
0.8784	High Similarity	NPC475096
0.8784	High Similarity	NPC476869
0.8784	High Similarity	NPC226722
0.8784	High Similarity	NPC476866
0.8784	High Similarity	NPC476868
0.8784	High Similarity	NPC85624
0.8782	High Similarity	NPC311803
0.8782	High Similarity	NPC472859
0.8782	High Similarity	NPC25389
0.8776	High Similarity	NPC7439
0.8776	High Similarity	NPC256555
0.8776	High Similarity	NPC236419
0.8776	High Similarity	NPC91492
0.8776	High Similarity	NPC34245
0.8776	High Similarity	NPC110067
0.8774	High Similarity	NPC287872
0.8774	High Similarity	NPC74319
0.8767	High Similarity	NPC469661
0.8759	High Similarity	NPC226005
0.8759	High Similarity	NPC98777
0.8759	High Similarity	NPC212770
0.8758	High Similarity	NPC8712
0.8758	High Similarity	NPC163165
0.875	High Similarity	NPC166180
0.875	High Similarity	NPC203230
0.875	High Similarity	NPC242028
0.8741	High Similarity	NPC87696
0.8741	High Similarity	NPC7163
0.8733	High Similarity	NPC169510
0.8732	High Similarity	NPC137669
0.8732	High Similarity	NPC470270
0.8732	High Similarity	NPC299144
0.8725	High Similarity	NPC40222
0.8725	High Similarity	NPC125755
0.8725	High Similarity	NPC268515
0.8725	High Similarity	NPC476865
0.8725	High Similarity	NPC99515
0.8725	High Similarity	NPC190714
0.8718	High Similarity	NPC119125
0.8718	High Similarity	NPC166277
0.8716	High Similarity	NPC469313
0.8716	High Similarity	NPC76176
0.8716	High Similarity	NPC138227
0.8716	High Similarity	NPC476867
0.8716	High Similarity	NPC168579
0.8707	High Similarity	NPC189115
0.8707	High Similarity	NPC469559
0.8704	High Similarity	NPC84482
0.8704	High Similarity	NPC169645
0.8693	High Similarity	NPC310661
0.8693	High Similarity	NPC105827
0.869	High Similarity	NPC124149
0.869	High Similarity	NPC38874
0.8681	High Similarity	NPC240915
0.8671	High Similarity	NPC132895
0.8671	High Similarity	NPC241341
0.8671	High Similarity	NPC233018
0.8671	High Similarity	NPC49074
0.8671	High Similarity	NPC277021
0.8671	High Similarity	NPC36437
0.8667	High Similarity	NPC296377
0.8667	High Similarity	NPC231149
0.8667	High Similarity	NPC87950
0.8667	High Similarity	NPC471764
0.8662	High Similarity	NPC217950
0.8658	High Similarity	NPC277867
0.8658	High Similarity	NPC100998
0.8658	High Similarity	NPC252292
0.8658	High Similarity	NPC161700
0.8658	High Similarity	NPC34927
0.8658	High Similarity	NPC476382
0.8658	High Similarity	NPC34587
0.8654	High Similarity	NPC289811
0.8654	High Similarity	NPC160780
0.8649	High Similarity	NPC230157
0.8649	High Similarity	NPC37793
0.8627	High Similarity	NPC289967
0.8627	High Similarity	NPC472611
0.8627	High Similarity	NPC472612
0.8621	High Similarity	NPC164857
0.8621	High Similarity	NPC471664
0.8621	High Similarity	NPC471665
0.8618	High Similarity	NPC476871
0.8611	High Similarity	NPC251981
0.8611	High Similarity	NPC13745
0.8611	High Similarity	NPC107478
0.8611	High Similarity	NPC48863
0.8609	High Similarity	NPC139839
0.8609	High Similarity	NPC48366
0.8608	High Similarity	NPC90905
0.8608	High Similarity	NPC4013
0.8601	High Similarity	NPC162093
0.8599	High Similarity	NPC239966
0.8599	High Similarity	NPC203020
0.8592	High Similarity	NPC244799
0.8592	High Similarity	NPC240722
0.8591	High Similarity	NPC110063
0.8591	High Similarity	NPC25292
0.8591	High Similarity	NPC185127
0.8591	High Similarity	NPC473045
0.859	High Similarity	NPC1913
0.8582	High Similarity	NPC146540
0.8582	High Similarity	NPC232880
0.8582	High Similarity	NPC40377
0.8581	High Similarity	NPC469564
0.8581	High Similarity	NPC193722
0.8581	High Similarity	NPC278469
0.858	High Similarity	NPC172807
0.858	High Similarity	NPC254540
0.858	High Similarity	NPC211594
0.8571	High Similarity	NPC78809
0.8571	High Similarity	NPC246893
0.8562	High Similarity	NPC126206
0.8553	High Similarity	NPC121290
0.8553	High Similarity	NPC94777
0.8552	High Similarity	NPC73071
0.8552	High Similarity	NPC55040

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 NPC313334 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	967
0.2-0.3	2164
0.3-0.4	2624
0.4-0.5	1728
0.5-0.6	854
0.6-0.7	268
0.7-0.8	119
0.8-0.85	22
0.85-0.9	10
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1653	Approved
0.8476	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1613	Approved
0.8345	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD3818	Discontinued
0.8255	Intermediate Similarity	NPD7266	Discontinued
0.8232	Intermediate Similarity	NPD7054	Approved
0.8182	Intermediate Similarity	NPD7472	Approved
0.8085	Intermediate Similarity	NPD1091	Approved
0.8072	Intermediate Similarity	NPD7074	Phase 3
0.8069	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1652	Phase 2
0.8024	Intermediate Similarity	NPD6797	Phase 2
0.8012	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7251	Discontinued
0.7929	Intermediate Similarity	NPD7808	Phase 3
0.7891	Intermediate Similarity	NPD3027	Phase 3
0.7832	Intermediate Similarity	NPD422	Phase 1
0.7826	Intermediate Similarity	NPD2801	Approved
0.7798	Intermediate Similarity	NPD5844	Phase 1
0.7764	Intermediate Similarity	NPD1934	Approved
0.7744	Intermediate Similarity	NPD6234	Discontinued
0.7738	Intermediate Similarity	NPD7228	Approved
0.7716	Intermediate Similarity	NPD1465	Phase 2
0.7682	Intermediate Similarity	NPD5124	Phase 1
0.7682	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD5402	Approved
0.7669	Intermediate Similarity	NPD3817	Phase 2
0.7661	Intermediate Similarity	NPD6559	Discontinued
0.7654	Intermediate Similarity	NPD37	Approved
0.7651	Intermediate Similarity	NPD7199	Phase 2
0.7622	Intermediate Similarity	NPD4965	Approved
0.7622	Intermediate Similarity	NPD4966	Approved
0.7622	Intermediate Similarity	NPD4967	Phase 2
0.7619	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6166	Phase 2
0.7619	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1511	Approved
0.758	Intermediate Similarity	NPD6190	Approved
0.7558	Intermediate Similarity	NPD7685	Pre-registration
0.7514	Intermediate Similarity	NPD7549	Discontinued
0.75	Intermediate Similarity	NPD1512	Approved
0.7485	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6674	Discontinued
0.7451	Intermediate Similarity	NPD230	Phase 1
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.7423	Intermediate Similarity	NPD4380	Phase 2
0.741	Intermediate Similarity	NPD3882	Suspended
0.7365	Intermediate Similarity	NPD7075	Discontinued
0.7347	Intermediate Similarity	NPD1610	Phase 2
0.7346	Intermediate Similarity	NPD5403	Approved
0.7346	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD447	Suspended
0.7303	Intermediate Similarity	NPD6843	Phase 3
0.7303	Intermediate Similarity	NPD6842	Approved
0.7303	Intermediate Similarity	NPD6841	Approved
0.7289	Intermediate Similarity	NPD8455	Phase 2
0.7288	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2861	Phase 2
0.7279	Intermediate Similarity	NPD3496	Discontinued
0.7267	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1357	Approved
0.7257	Intermediate Similarity	NPD7240	Approved
0.7248	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4908	Phase 1
0.7229	Intermediate Similarity	NPD6801	Discontinued
0.7225	Intermediate Similarity	NPD3751	Discontinued
0.7222	Intermediate Similarity	NPD5401	Approved
0.7188	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3750	Approved
0.7188	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5494	Approved
0.7171	Intermediate Similarity	NPD3018	Phase 2
0.717	Intermediate Similarity	NPD1549	Phase 2
0.7167	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1933	Approved
0.7114	Intermediate Similarity	NPD3705	Approved
0.7107	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6232	Discontinued
0.7093	Intermediate Similarity	NPD3787	Discontinued
0.7088	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3225	Approved
0.7083	Intermediate Similarity	NPD7819	Suspended
0.7079	Intermediate Similarity	NPD8312	Approved
0.7079	Intermediate Similarity	NPD8313	Approved
0.7063	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD228	Approved
0.7055	Intermediate Similarity	NPD6799	Approved
0.7051	Intermediate Similarity	NPD4060	Phase 1
0.7035	Intermediate Similarity	NPD8127	Discontinued
0.7032	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2982	Phase 2
0.702	Intermediate Similarity	NPD4749	Approved
0.702	Intermediate Similarity	NPD2983	Phase 2
0.7018	Intermediate Similarity	NPD919	Approved
0.7013	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4340	Discontinued
0.6988	Remote Similarity	NPD3687	Approved
0.6988	Remote Similarity	NPD3686	Approved
0.6987	Remote Similarity	NPD6233	Phase 2
0.6981	Remote Similarity	NPD1510	Phase 2
0.6975	Remote Similarity	NPD4628	Phase 3
0.6971	Remote Similarity	NPD7473	Discontinued
0.6964	Remote Similarity	NPD7411	Suspended
0.6954	Remote Similarity	NPD2981	Phase 2
0.6952	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2935	Discontinued
0.6923	Remote Similarity	NPD1296	Phase 2
0.6918	Remote Similarity	NPD7097	Phase 1
0.6909	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1358	Approved
0.6901	Remote Similarity	NPD290	Approved
0.6895	Remote Similarity	NPD7680	Approved
0.6879	Remote Similarity	NPD9697	Approved
0.6875	Remote Similarity	NPD3748	Approved
0.6871	Remote Similarity	NPD6671	Approved
0.6867	Remote Similarity	NPD1778	Approved
0.6867	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4625	Phase 3
0.6852	Remote Similarity	NPD2424	Discontinued
0.6848	Remote Similarity	NPD4357	Discontinued
0.6842	Remote Similarity	NPD9269	Phase 2
0.6842	Remote Similarity	NPD5353	Approved
0.6839	Remote Similarity	NPD7585	Approved
0.6839	Remote Similarity	NPD1247	Approved
0.6839	Remote Similarity	NPD9494	Approved
0.6832	Remote Similarity	NPD2796	Approved
0.6818	Remote Similarity	NPD1203	Approved
0.6818	Remote Similarity	NPD2797	Approved
0.6815	Remote Similarity	NPD6798	Discontinued
0.6813	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6599	Discontinued
0.6802	Remote Similarity	NPD7768	Phase 2
0.679	Remote Similarity	NPD5763	Approved
0.679	Remote Similarity	NPD5762	Approved
0.6788	Remote Similarity	NPD7583	Approved
0.6788	Remote Similarity	NPD5058	Phase 3
0.6782	Remote Similarity	NPD5677	Discontinued
0.6779	Remote Similarity	NPD5536	Phase 2
0.677	Remote Similarity	NPD7033	Discontinued
0.6765	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6653	Approved
0.6744	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7783	Phase 2
0.6735	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD9717	Approved
0.673	Remote Similarity	NPD1558	Phase 1
0.6723	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7435	Discontinued
0.6713	Remote Similarity	NPD968	Approved
0.6709	Remote Similarity	NPD3268	Approved
0.6707	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4678	Approved
0.6706	Remote Similarity	NPD4675	Approved
0.6687	Remote Similarity	NPD3540	Phase 1
0.6687	Remote Similarity	NPD6355	Discontinued
0.6687	Remote Similarity	NPD1375	Discontinued
0.6686	Remote Similarity	NPD2978	Approved
0.6686	Remote Similarity	NPD2977	Approved
0.6685	Remote Similarity	NPD7039	Approved
0.6685	Remote Similarity	NPD7038	Approved
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4110	Phase 3
0.6667	Remote Similarity	NPD7843	Approved
0.6667	Remote Similarity	NPD1535	Discovery
0.6649	Remote Similarity	NPD6782	Approved
0.6649	Remote Similarity	NPD6778	Approved
0.6649	Remote Similarity	NPD6777	Approved
0.6649	Remote Similarity	NPD6781	Approved
0.6649	Remote Similarity	NPD6780	Approved
0.6649	Remote Similarity	NPD6776	Approved
0.6649	Remote Similarity	NPD6779	Approved
0.6648	Remote Similarity	NPD6959	Discontinued
0.6647	Remote Similarity	NPD1774	Approved
0.6647	Remote Similarity	NPD7213	Phase 3
0.6647	Remote Similarity	NPD7212	Phase 2
0.6647	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7095	Approved
0.6645	Remote Similarity	NPD8651	Approved
0.6645	Remote Similarity	NPD4626	Approved
0.6644	Remote Similarity	NPD7157	Approved
0.6633	Remote Similarity	NPD8151	Discontinued
0.6627	Remote Similarity	NPD920	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