NPASS Compound

Structure

CID175890 OpenBabel06191715552D 43 49 0 0 1 0 0 0 0 0999 V2000 2.2280 -3.1422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5822 2.9932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2280 2.7030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6224 -3.1865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3474 -2.2988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0836 -2.2564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0947 -3.4355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4156 -2.6589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0515 -3.1222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1782 0.0473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0717 -0.7067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4601 -0.2964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0717 -1.6809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1435 -1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3042 -2.2589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9228 -2.6161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4112 0.4392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2280 0.7546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1442 -0.1266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0407 -2.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1274 -2.0696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7338 0.0412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2280 -0.2196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4853 -3.4997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6237 -0.4591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9693 -0.9293 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3843 -1.6809 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2856 -3.5272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5518 -3.0665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8989 0.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5827 0.0321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3843 1.2417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3843 -0.7067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5406 0.7546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5406 -0.2196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3671 -0.7310 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.2280 -2.1680 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2495 -4.5008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3030 1.2417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0397 2.1840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3843 2.2159 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0547 -3.3721 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 37 1 0 0 0 0 2 40 1 0 0 0 0 3 41 1 0 0 0 0 4 7 1 0 0 0 0 4 20 2 0 0 0 0 5 8 2 0 0 0 0 5 20 1 0 0 0 0 6 9 2 0 0 0 0 6 21 1 0 0 0 0 7 24 2 0 0 0 0 8 24 1 0 0 0 0 9 28 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 36 1 0 0 0 0 13 37 1 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 16 29 1 0 0 0 0 17 22 2 0 0 0 0 17 30 1 0 0 0 0 18 23 2 0 0 0 0 18 32 1 0 0 0 0 19 25 2 0 0 0 0 19 31 1 0 0 0 0 22 25 1 0 0 0 0 23 33 1 0 0 0 0 24 42 1 0 0 0 0 25 26 1 0 0 0 0 26 14 1 1 0 0 0 26 36 1 0 0 0 0 27 15 1 1 0 0 0 27 33 1 0 0 0 0 27 37 1 0 0 0 0 28 29 2 0 0 0 0 28 38 1 0 0 0 0 29 42 1 0 0 0 0 30 31 2 0 0 0 0 30 40 1 0 0 0 0 31 43 1 0 0 0 0 32 34 2 0 0 0 0 32 41 1 0 0 0 0 33 35 2 0 0 0 0 34 35 1 0 0 0 0 34 39 1 0 0 0 0 35 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.26
Volume:	597.118
LogP:	5.464
LogD:	3.666
LogS:	-4.083
# Rotatable Bonds:	2
TPSA:	92.65
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.258
Synthetic Accessibility Score:	5.796
Fsp3:	0.314
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.863
MDCK Permeability:	1.5410529158543795e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.619
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.186
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	72.26887512207031%
Volume Distribution (VD):	0.737
Pgp-substrate:	16.738872528076172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.176
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.407
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.948
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.94

ADMET: Excretion

Clearance (CL):	6.839
Half-life (T1/2):	0.486

ADMET: Toxicity

hERG Blockers:	0.939
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.521
AMES Toxicity:	0.23
Rat Oral Acute Toxicity:	0.347
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.928
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.366

Download Data

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

Natural Product: NPC175890

Natural Product ID:	NPC175890
*Common Name:**	Daphnoline
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AKGWXHYTRBFUAD-SXOMAYOGSA-N
Standard InCHI:	InChI=1S/C35H36N2O6/c1-37-13-11-23-18-32(41-3)34(39)35-33(23)27(37)15-20-4-7-24(8-5-20)42-29-16-21(6-9-28(29)38)14-26-25-19-31(43-35)30(40-2)17-22(25)10-12-36-26/h4-9,16-19,26-27,36,38-39H,10-15H2,1-3H3/t26-,27+/m1/s1
SMILES:	COc1cc2CCN[C@H]3c2cc1Oc1c2c(CCN([C@H]2Cc2ccc(Oc4cc(C3)ccc4O)cc2)C)cc(c1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2262848
PubChem CID:	261477
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23450	Chionographis japonica	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6471	Trillium camtschaticum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23450	Chionographis japonica	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5156	Hypoestes rosea	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7389	Rhodiola atuntsuensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6471	Trillium camtschaticum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6471	Trillium camtschaticum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7389	Rhodiola atuntsuensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6730	Crossopteryx febrifuga	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23450	Chionographis japonica	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24372	Artemisia palustris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6471	Trillium camtschaticum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19931	Pyrus x nivalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1516	Passiflora suberosa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5156	Hypoestes rosea	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1698	Glycyrrhiza inflata	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	>	50.0	ug.mL-1	PMID[482445]

☑ 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 NPC175890 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	373
0.1-0.2	1900
0.2-0.3	9591
0.3-0.4	8630
0.4-0.5	6149
0.5-0.6	9641
0.6-0.7	5278
0.7-0.8	841
0.8-0.85	159
0.85-0.9	48
0.9-0.95	44
0.95-1	43

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC82457
1.0	High Similarity	NPC48490
1.0	High Similarity	NPC274661
1.0	High Similarity	NPC11296
0.9941	High Similarity	NPC191132
0.9941	High Similarity	NPC60295
0.9704	High Similarity	NPC185639
0.9704	High Similarity	NPC251735
0.9704	High Similarity	NPC328155
0.9704	High Similarity	NPC271013
0.9704	High Similarity	NPC104196
0.9704	High Similarity	NPC290582
0.9704	High Similarity	NPC222661
0.9704	High Similarity	NPC311973
0.9704	High Similarity	NPC279228
0.9704	High Similarity	NPC7715
0.9704	High Similarity	NPC54654
0.9704	High Similarity	NPC49075
0.9704	High Similarity	NPC182052
0.9704	High Similarity	NPC42663
0.9704	High Similarity	NPC239824
0.9704	High Similarity	NPC90998
0.9704	High Similarity	NPC229373
0.9704	High Similarity	NPC223690
0.9704	High Similarity	NPC217748
0.9704	High Similarity	NPC15414
0.9704	High Similarity	NPC290005
0.9704	High Similarity	NPC181796
0.9704	High Similarity	NPC285931
0.9704	High Similarity	NPC8836
0.9704	High Similarity	NPC258657
0.9647	High Similarity	NPC167116
0.9647	High Similarity	NPC274716
0.9647	High Similarity	NPC254441
0.9645	High Similarity	NPC286119
0.9598	High Similarity	NPC256124
0.9588	High Similarity	NPC30779
0.9586	High Similarity	NPC475479
0.9586	High Similarity	NPC243454
0.9535	High Similarity	NPC116465
0.9535	High Similarity	NPC212237
0.9529	High Similarity	NPC239584
0.948	High Similarity	NPC22115
0.948	High Similarity	NPC275680
0.9425	High Similarity	NPC206900
0.9364	High Similarity	NPC302245
0.9364	High Similarity	NPC95426
0.9364	High Similarity	NPC16357
0.9318	High Similarity	NPC24260
0.931	High Similarity	NPC139783
0.931	High Similarity	NPC65312
0.929	High Similarity	NPC115284
0.929	High Similarity	NPC317439
0.929	High Similarity	NPC63646
0.929	High Similarity	NPC108434
0.929	High Similarity	NPC475215
0.929	High Similarity	NPC76682
0.929	High Similarity	NPC227060
0.929	High Similarity	NPC276890
0.929	High Similarity	NPC10908
0.929	High Similarity	NPC317145
0.929	High Similarity	NPC198498
0.9235	High Similarity	NPC129518
0.9235	High Similarity	NPC41376
0.9235	High Similarity	NPC12424
0.9235	High Similarity	NPC251580
0.9209	High Similarity	NPC478093
0.9205	High Similarity	NPC281581
0.9157	High Similarity	NPC30182
0.9157	High Similarity	NPC473589
0.9157	High Similarity	NPC478092
0.9157	High Similarity	NPC478091
0.9128	High Similarity	NPC293093
0.9053	High Similarity	NPC250846
0.9053	High Similarity	NPC268503
0.9053	High Similarity	NPC256012
0.9053	High Similarity	NPC264850
0.9053	High Similarity	NPC42549
0.9053	High Similarity	NPC13916
0.9053	High Similarity	NPC317272
0.9053	High Similarity	NPC240841
0.905	High Similarity	NPC85381
0.9045	High Similarity	NPC41122
0.9045	High Similarity	NPC318805
0.9011	High Similarity	NPC475654
0.8994	High Similarity	NPC24465
0.895	High Similarity	NPC234318
0.8947	High Similarity	NPC204908
0.8947	High Similarity	NPC83198
0.8935	High Similarity	NPC475393
0.892	High Similarity	NPC299990
0.892	High Similarity	NPC73492
0.8807	High Similarity	NPC474507
0.8793	High Similarity	NPC232386
0.8793	High Similarity	NPC152680
0.8793	High Similarity	NPC190783
0.8764	High Similarity	NPC302275
0.8757	High Similarity	NPC257269
0.8757	High Similarity	NPC230276
0.8715	High Similarity	NPC249996
0.8701	High Similarity	NPC40496
0.8701	High Similarity	NPC119068
0.8693	High Similarity	NPC173416
0.8693	High Similarity	NPC148709
0.8693	High Similarity	NPC476577
0.8678	High Similarity	NPC109925
0.8663	High Similarity	NPC4138
0.8663	High Similarity	NPC121275
0.8663	High Similarity	NPC254581
0.8663	High Similarity	NPC284183
0.8652	High Similarity	NPC195538
0.8639	High Similarity	NPC247639
0.8639	High Similarity	NPC25084
0.8626	High Similarity	NPC475597
0.8626	High Similarity	NPC473716
0.8603	High Similarity	NPC476202
0.858	High Similarity	NPC469817
0.858	High Similarity	NPC172765
0.858	High Similarity	NPC39701
0.858	High Similarity	NPC276588
0.858	High Similarity	NPC2413
0.858	High Similarity	NPC193949
0.858	High Similarity	NPC249797
0.858	High Similarity	NPC127674
0.858	High Similarity	NPC110416
0.858	High Similarity	NPC184026
0.858	High Similarity	NPC54379
0.858	High Similarity	NPC189266
0.858	High Similarity	NPC295691
0.858	High Similarity	NPC5238
0.858	High Similarity	NPC207757
0.858	High Similarity	NPC204828
0.858	High Similarity	NPC278799
0.8564	High Similarity	NPC14507
0.8564	High Similarity	NPC47077
0.8523	High Similarity	NPC239775
0.8521	High Similarity	NPC2295
0.8521	High Similarity	NPC477564
0.8506	High Similarity	NPC193853
0.8506	High Similarity	NPC223077
0.8506	High Similarity	NPC56887
0.8475	Intermediate Similarity	NPC477020
0.8475	Intermediate Similarity	NPC66341
0.8475	Intermediate Similarity	NPC192135
0.8466	Intermediate Similarity	NPC69712
0.8466	Intermediate Similarity	NPC26240
0.8466	Intermediate Similarity	NPC118274
0.8466	Intermediate Similarity	NPC477562
0.8466	Intermediate Similarity	NPC168753
0.8448	Intermediate Similarity	NPC209377
0.8418	Intermediate Similarity	NPC10871
0.8415	Intermediate Similarity	NPC186546
0.8415	Intermediate Similarity	NPC476576
0.8402	Intermediate Similarity	NPC76213
0.8402	Intermediate Similarity	NPC277669
0.8352	Intermediate Similarity	NPC204947
0.8343	Intermediate Similarity	NPC151895
0.8343	Intermediate Similarity	NPC220858
0.8343	Intermediate Similarity	NPC88249
0.8343	Intermediate Similarity	NPC192768
0.8343	Intermediate Similarity	NPC97221
0.8333	Intermediate Similarity	NPC60186
0.8295	Intermediate Similarity	NPC81247
0.8295	Intermediate Similarity	NPC476573
0.8295	Intermediate Similarity	NPC35627
0.8284	Intermediate Similarity	NPC477565
0.8284	Intermediate Similarity	NPC103379
0.8284	Intermediate Similarity	NPC60538
0.8284	Intermediate Similarity	NPC207824
0.8283	Intermediate Similarity	NPC82056
0.828	Intermediate Similarity	NPC476565
0.8276	Intermediate Similarity	NPC205255
0.8276	Intermediate Similarity	NPC230956
0.8276	Intermediate Similarity	NPC119649
0.8276	Intermediate Similarity	NPC235143
0.8276	Intermediate Similarity	NPC271388
0.8261	Intermediate Similarity	NPC57036
0.8256	Intermediate Similarity	NPC187022
0.8256	Intermediate Similarity	NPC80129
0.8249	Intermediate Similarity	NPC12053
0.8249	Intermediate Similarity	NPC474931
0.8249	Intermediate Similarity	NPC205421
0.8249	Intermediate Similarity	NPC81218
0.8249	Intermediate Similarity	NPC158376
0.8249	Intermediate Similarity	NPC145832
0.8249	Intermediate Similarity	NPC306555
0.8249	Intermediate Similarity	NPC117188
0.8239	Intermediate Similarity	NPC253043
0.8239	Intermediate Similarity	NPC276944
0.8239	Intermediate Similarity	NPC196447
0.8239	Intermediate Similarity	NPC306843
0.8239	Intermediate Similarity	NPC232514
0.8239	Intermediate Similarity	NPC212794
0.8239	Intermediate Similarity	NPC96603
0.8239	Intermediate Similarity	NPC136508
0.8239	Intermediate Similarity	NPC238530
0.8239	Intermediate Similarity	NPC13504
0.8239	Intermediate Similarity	NPC477563
0.8239	Intermediate Similarity	NPC78222
0.8229	Intermediate Similarity	NPC79402

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 NPC175890 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	749
0.2-0.3	1199
0.3-0.4	2143
0.4-0.5	2534
0.5-0.6	1551
0.6-0.7	650
0.7-0.8	116
0.8-0.85	5
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9704	High Similarity	NPD8053	Approved
0.9704	High Similarity	NPD8054	Approved
0.929	High Similarity	NPD8099	Discontinued
0.929	High Similarity	NPD8251	Approved
0.929	High Similarity	NPD8252	Approved
0.9235	High Similarity	NPD8156	Discontinued
0.8701	High Similarity	NPD8453	Clinical (unspecified phase)
0.8351	Intermediate Similarity	NPD8095	Phase 1
0.8256	Intermediate Similarity	NPD7298	Approved
0.8166	Intermediate Similarity	NPD4584	Approved
0.8114	Intermediate Similarity	NPD6788	Approved
0.7968	Intermediate Similarity	NPD7906	Approved
0.7953	Intermediate Similarity	NPD1424	Approved
0.7886	Intermediate Similarity	NPD4772	Phase 2
0.7886	Intermediate Similarity	NPD4773	Phase 2
0.7861	Intermediate Similarity	NPD6031	Approved
0.7861	Intermediate Similarity	NPD6030	Approved
0.7812	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD6071	Discontinued
0.7765	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7831	Phase 2
0.7765	Intermediate Similarity	NPD7833	Phase 2
0.7754	Intermediate Similarity	NPD7311	Approved
0.7754	Intermediate Similarity	NPD7310	Approved
0.7754	Intermediate Similarity	NPD7313	Approved
0.7754	Intermediate Similarity	NPD7312	Approved
0.7733	Intermediate Similarity	NPD3845	Phase 1
0.7713	Intermediate Similarity	NPD7309	Approved
0.7709	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD2489	Approved
0.7705	Intermediate Similarity	NPD27	Approved
0.7692	Intermediate Similarity	NPD3051	Approved
0.767	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD4578	Approved
0.766	Intermediate Similarity	NPD4577	Approved
0.765	Intermediate Similarity	NPD2969	Approved
0.765	Intermediate Similarity	NPD2970	Approved
0.7644	Intermediate Similarity	NPD7447	Phase 1
0.7644	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD6107	Approved
0.7632	Intermediate Similarity	NPD4663	Approved
0.7588	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7598	Phase 2
0.7582	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD2560	Approved
0.7556	Intermediate Similarity	NPD2563	Approved
0.7529	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7549	Discontinued
0.75	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4010	Discontinued
0.7486	Intermediate Similarity	NPD7213	Phase 3
0.7486	Intermediate Similarity	NPD7212	Phase 2
0.7477	Intermediate Similarity	NPD8152	Approved
0.7477	Intermediate Similarity	NPD8153	Approved
0.7435	Intermediate Similarity	NPD6851	Approved
0.7435	Intermediate Similarity	NPD6853	Approved
0.7427	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2898	Approved
0.7415	Intermediate Similarity	NPD7827	Phase 1
0.7407	Intermediate Similarity	NPD6297	Approved
0.7394	Intermediate Similarity	NPD6042	Phase 2
0.7394	Intermediate Similarity	NPD42	Phase 2
0.7386	Intermediate Similarity	NPD2420	Approved
0.7386	Intermediate Similarity	NPD2421	Approved
0.7377	Intermediate Similarity	NPD4055	Discovery
0.7371	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3060	Approved
0.7356	Intermediate Similarity	NPD4162	Approved
0.7337	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4675	Approved
0.7333	Intermediate Similarity	NPD4678	Approved
0.733	Intermediate Similarity	NPD7124	Phase 2
0.7308	Intermediate Similarity	NPD4585	Approved
0.7308	Intermediate Similarity	NPD2977	Approved
0.7308	Intermediate Similarity	NPD2978	Approved
0.7297	Intermediate Similarity	NPD5677	Discontinued
0.7293	Intermediate Similarity	NPD6072	Discontinued
0.7278	Intermediate Similarity	NPD4017	Approved
0.7273	Intermediate Similarity	NPD5160	Discontinued
0.7273	Intermediate Similarity	NPD5241	Discontinued
0.7273	Intermediate Similarity	NPD2677	Approved
0.7264	Intermediate Similarity	NPD2494	Approved
0.7264	Intermediate Similarity	NPD3452	Approved
0.7264	Intermediate Similarity	NPD3450	Approved
0.7264	Intermediate Similarity	NPD2493	Approved
0.7263	Intermediate Similarity	NPD3641	Approved
0.7263	Intermediate Similarity	NPD7479	Phase 2
0.7263	Intermediate Similarity	NPD3639	Approved
0.7263	Intermediate Similarity	NPD3640	Phase 3
0.7258	Intermediate Similarity	NPD7802	Discontinued
0.7247	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD2488	Approved
0.7245	Intermediate Similarity	NPD2490	Approved
0.7241	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4481	Phase 3
0.7219	Intermediate Similarity	NPD4166	Phase 2
0.7213	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4873	Discontinued
0.7207	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4666	Phase 3
0.7183	Intermediate Similarity	NPD6997	Phase 2
0.7182	Intermediate Similarity	NPD4005	Discontinued
0.7167	Intermediate Similarity	NPD5976	Discontinued
0.7165	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4582	Approved
0.7157	Intermediate Similarity	NPD4583	Approved
0.7157	Intermediate Similarity	NPD4040	Phase 1
0.7151	Intermediate Similarity	NPD5709	Phase 3
0.7143	Intermediate Similarity	NPD7047	Phase 3
0.7135	Intermediate Similarity	NPD4475	Approved
0.7135	Intermediate Similarity	NPD4474	Approved
0.7123	Intermediate Similarity	NPD6723	Discontinued
0.712	Intermediate Similarity	NPD5773	Approved
0.712	Intermediate Similarity	NPD5772	Approved
0.7119	Intermediate Similarity	NPD6748	Discontinued
0.7108	Intermediate Similarity	NPD4002	Approved
0.7108	Intermediate Similarity	NPD4004	Approved
0.7097	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1774	Approved
0.7088	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6618	Phase 2
0.7076	Intermediate Similarity	NPD5718	Phase 2
0.7072	Intermediate Similarity	NPD2122	Discontinued
0.7069	Intermediate Similarity	NPD2200	Suspended
0.7065	Intermediate Similarity	NPD3384	Approved
0.7065	Intermediate Similarity	NPD2973	Approved
0.7065	Intermediate Similarity	NPD2974	Approved
0.7065	Intermediate Similarity	NPD2975	Approved
0.7065	Intermediate Similarity	NPD3383	Approved
0.7065	Intermediate Similarity	NPD3382	Approved
0.7065	Intermediate Similarity	NPD5722	Discontinued
0.7062	Intermediate Similarity	NPD5177	Phase 3
0.7059	Intermediate Similarity	NPD5006	Approved
0.7059	Intermediate Similarity	NPD5005	Approved
0.7059	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4123	Phase 3
0.7047	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5313	Approved
0.7031	Intermediate Similarity	NPD5312	Approved
0.7029	Intermediate Similarity	NPD2155	Approved
0.7029	Intermediate Similarity	NPD2156	Approved
0.7029	Intermediate Similarity	NPD2154	Approved
0.7022	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7466	Approved
0.7017	Intermediate Similarity	NPD7526	Approved
0.7017	Intermediate Similarity	NPD6090	Discontinued
0.7017	Intermediate Similarity	NPD52	Approved
0.7017	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7153	Discontinued
0.7	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3124	Discontinued
0.7	Intermediate Similarity	NPD6087	Phase 1
0.6995	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1613	Approved
0.6994	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD3053	Approved
0.6982	Remote Similarity	NPD3055	Approved
0.6974	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD5720	Discontinued
0.6973	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5061	Approved
0.6966	Remote Similarity	NPD5062	Approved
0.6961	Remote Similarity	NPD4580	Approved
0.6959	Remote Similarity	NPD4908	Phase 1
0.6944	Remote Similarity	NPD3122	Phase 3
0.694	Remote Similarity	NPD3686	Approved
0.694	Remote Similarity	NPD3687	Approved
0.6939	Remote Similarity	NPD2971	Approved
0.6939	Remote Similarity	NPD2968	Approved
0.6939	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2843	Phase 2
0.6935	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2845	Phase 2
0.6927	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7039	Approved
0.6923	Remote Similarity	NPD5310	Approved
0.6923	Remote Similarity	NPD5311	Approved
0.6923	Remote Similarity	NPD7038	Approved
0.6914	Remote Similarity	NPD3052	Approved
0.6914	Remote Similarity	NPD2568	Approved
0.6914	Remote Similarity	NPD817	Approved
0.6914	Remote Similarity	NPD3054	Approved
0.6914	Remote Similarity	NPD823	Approved
0.6914	Remote Similarity	NPD5314	Approved
0.69	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4605	Approved
0.6897	Remote Similarity	NPD4604	Approved
0.6891	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3692	Discontinued
0.6888	Remote Similarity	NPD3936	Clinical (unspecified phase)

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