NPASS Compound

Structure

CID190185 OpenBabel06191715572D 37 40 0 0 1 0 0 0 0 0999 V2000 1.7744 -5.6216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0547 -5.9186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2019 1.0092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1972 0.7332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1576 -1.2288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6574 -4.2808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3293 -1.2277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2047 0.7332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9823 -0.2242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8288 -5.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2019 0.0016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3293 -0.5022 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7010 -1.5905 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7010 1.6058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2882 -3.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5054 -0.0498 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3145 -2.2950 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0726 -0.5022 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1461 -1.6237 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2020 -0.2113 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9444 -2.5819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4149 -1.3216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7010 -0.1394 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0726 -1.2277 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5168 -0.8649 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0745 -0.5022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2047 2.4783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6934 1.6058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0623 -4.5777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7296 0.9325 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8302 0.5765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 -3.5893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4685 -2.3277 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2595 -0.7721 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 1.5614 -2.2684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4596 -2.9399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 5 34 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 8 23 1 0 0 0 0 9 35 1 0 0 0 0 11 12 1 0 0 0 0 11 26 2 0 0 0 0 12 23 1 6 0 0 0 13 24 1 1 0 0 0 13 36 1 0 0 0 0 14 27 2 0 0 0 0 14 28 1 0 0 0 0 15 29 2 0 0 0 0 15 37 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 16 30 1 6 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 17 37 1 6 0 0 0 18 23 1 6 0 0 0 18 24 1 0 0 0 0 19 24 1 1 0 0 0 19 25 1 0 0 0 0 20 25 1 1 0 0 0 20 31 1 0 0 0 0 21 32 2 0 0 0 0 21 36 1 0 0 0 0 22 33 2 0 0 0 0 22 34 1 0 0 0 0 23 4 1 6 0 0 0 24 9 1 6 0 0 0 25 22 1 6 0 0 0 25 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	524.19
Volume:	496.394
LogP:	0.77
LogD:	-0.252
LogS:	-3.026
# Rotatable Bonds:	8
TPSA:	182.96
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.236
Synthetic Accessibility Score:	6.406
Fsp3:	0.72
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.734
MDCK Permeability:	9.671824955148622e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.13
20% Bioavailability (F20%):	0.758
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086
Plasma Protein Binding (PPB):	36.062705993652344%
Volume Distribution (VD):	0.265
Pgp-substrate:	46.55469512939453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.27
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	2.664
Half-life (T1/2):	0.901

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.562
Drug-inuced Liver Injury (DILI):	0.92
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.356
Maximum Recommended Daily Dose:	0.494
Skin Sensitization:	0.195
Carcinogencity:	0.045
Eye Corrosion:	0.005
Eye Irritation:	0.033
Respiratory Toxicity:	0.438

Download Data

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

Natural Product: NPC190185

Natural Product ID:	NPC190185
*Common Name:**	Bruceanic Acid E
IUPAC Name:	n.a.
Synonyms:	Bruceanic Acid E
Standard InCHIKey:	USQBKJMZGOZWID-AYJGHYFRSA-N
Standard InCHI:	InChI=1S/C25H32O12/c1-10(2)6-15(29)37-17-19-24-9-35-25(19,22(33)34-5)20(31)16(30)18(24)23(4,8-14(27)28)12(11(3)26)7-13(24)36-21(17)32/h6,12-13,16-20,30-31H,7-9H2,1-5H3,(H,27,28)/t12-,13+,16+,17+,18+,19+,20-,23-,24+,25-/m0/s1
SMILES:	CC(=CC(=O)O[C@@H]1[C@@H]2[C@]34CO[C@@]2([C@H]([C@@H]([C@@H]4[C@@](C)(CC(=O)O)[C@@H](C[C@H]3OC1=O)C(=O)C)O)O)C(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2037032
PubChem CID:	70681802
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*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
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/0031-9422(96)00258-0]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S1383-5769(99)00023-9]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10086989]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1512598]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15165151]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15949825]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	fruit	Indonesia	n.a.	PMID[17896817]
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18723353]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	Vietnam	n.a.	PMID[19026551]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20050684]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22506620]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26522747]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6481366]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561896]
NPO211	Aplysina cauliformis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350091]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12089	Trifolium alexandrinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11432	Centrolobium tomentosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12717	Parmelia metastrigosa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9203	Cephalonomia gallicola	Species	Bethylidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26718	Chelidonura fulvipunctata	Species	Aglajidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO211	Aplysina cauliformis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11084	Asplenium normale	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14749	Lippia carviodora	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14150	Solanum jamaicense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11637	Psilostrophe cooperi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5303	Castanea crenata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12944	Sideritis tragoriganum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14528	Pneumatospora obcoronata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3164	Yponomeuta malinellus	Species	Yponomeutidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14845	Ceratophyllum submersum	Species	Ceratophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10818	Carpobrotus edulis	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1641	Amycolatopsis azurea	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12089	Trifolium alexandrinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11873	Oecophylla smaragdina	Species	Formicidae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[497098]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[497098]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[497098]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[497098]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[497098]

☑ 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 NPC190185 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	295
0.1-0.2	1871
0.2-0.3	5352
0.3-0.4	8155
0.4-0.5	11719
0.5-0.6	7453
0.6-0.7	5486
0.7-0.8	2162
0.8-0.85	139
0.85-0.9	36
0.9-0.95	19
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC213084
0.9906	High Similarity	NPC299849
0.9811	High Similarity	NPC94509
0.9722	High Similarity	NPC470778
0.9722	High Similarity	NPC146432
0.963	High Similarity	NPC89929
0.9375	High Similarity	NPC470779
0.9211	High Similarity	NPC18945
0.9211	High Similarity	NPC265557
0.9211	High Similarity	NPC91693
0.9211	High Similarity	NPC105926
0.913	High Similarity	NPC476729
0.9123	High Similarity	NPC312833
0.9043	High Similarity	NPC67251
0.8966	High Similarity	NPC24651
0.8772	High Similarity	NPC17772
0.8684	High Similarity	NPC473590
0.8655	High Similarity	NPC476008
0.8644	High Similarity	NPC470922
0.8609	High Similarity	NPC470776
0.8596	High Similarity	NPC328374
0.8596	High Similarity	NPC96312
0.8596	High Similarity	NPC251236
0.8596	High Similarity	NPC40632
0.8596	High Similarity	NPC16081
0.8596	High Similarity	NPC173686
0.8584	High Similarity	NPC477126
0.8571	High Similarity	NPC477745
0.8534	High Similarity	NPC470777
0.8522	High Similarity	NPC122033
0.8522	High Similarity	NPC470854
0.8522	High Similarity	NPC287343
0.8522	High Similarity	NPC474654
0.8522	High Similarity	NPC97908
0.8512	High Similarity	NPC476851
0.8509	High Similarity	NPC473798
0.8509	High Similarity	NPC323821
0.8509	High Similarity	NPC143268
0.8509	High Similarity	NPC268238
0.8509	High Similarity	NPC45218
0.8468	Intermediate Similarity	NPC289702
0.8468	Intermediate Similarity	NPC262813
0.8468	Intermediate Similarity	NPC208461
0.8462	Intermediate Similarity	NPC109607
0.8462	Intermediate Similarity	NPC107338
0.8455	Intermediate Similarity	NPC168879
0.8448	Intermediate Similarity	NPC297179
0.8448	Intermediate Similarity	NPC251310
0.8443	Intermediate Similarity	NPC476852
0.8435	Intermediate Similarity	NPC474734
0.843	Intermediate Similarity	NPC476859
0.8421	Intermediate Similarity	NPC49451
0.8407	Intermediate Similarity	NPC157476
0.84	Intermediate Similarity	NPC141215
0.84	Intermediate Similarity	NPC190065
0.84	Intermediate Similarity	NPC251998
0.84	Intermediate Similarity	NPC471089
0.8376	Intermediate Similarity	NPC475775
0.8376	Intermediate Similarity	NPC476529
0.8374	Intermediate Similarity	NPC102316
0.8362	Intermediate Similarity	NPC470775
0.8362	Intermediate Similarity	NPC176513
0.8361	Intermediate Similarity	NPC476854
0.8333	Intermediate Similarity	NPC295885
0.8333	Intermediate Similarity	NPC140045
0.8333	Intermediate Similarity	NPC596
0.8319	Intermediate Similarity	NPC100908
0.8305	Intermediate Similarity	NPC112038
0.8293	Intermediate Similarity	NPC476855
0.8291	Intermediate Similarity	NPC188667
0.8291	Intermediate Similarity	NPC204552
0.8276	Intermediate Similarity	NPC235539
0.8276	Intermediate Similarity	NPC207217
0.8276	Intermediate Similarity	NPC134869
0.8276	Intermediate Similarity	NPC152199
0.8261	Intermediate Similarity	NPC208998
0.8261	Intermediate Similarity	NPC7921
0.8235	Intermediate Similarity	NPC102822
0.8235	Intermediate Similarity	NPC477046
0.8205	Intermediate Similarity	NPC58662
0.8197	Intermediate Similarity	NPC470780
0.819	Intermediate Similarity	NPC474906
0.819	Intermediate Similarity	NPC18547
0.8174	Intermediate Similarity	NPC269530
0.8174	Intermediate Similarity	NPC474516
0.8151	Intermediate Similarity	NPC109973
0.8151	Intermediate Similarity	NPC472004
0.8145	Intermediate Similarity	NPC476862
0.8145	Intermediate Similarity	NPC476863
0.813	Intermediate Similarity	NPC188291
0.812	Intermediate Similarity	NPC470628
0.812	Intermediate Similarity	NPC259306
0.812	Intermediate Similarity	NPC270478
0.812	Intermediate Similarity	NPC474046
0.8115	Intermediate Similarity	NPC181999
0.811	Intermediate Similarity	NPC243014
0.8103	Intermediate Similarity	NPC198539
0.8087	Intermediate Similarity	NPC469656
0.8087	Intermediate Similarity	NPC171888
0.8087	Intermediate Similarity	NPC474846
0.8087	Intermediate Similarity	NPC469655
0.8087	Intermediate Similarity	NPC146945
0.808	Intermediate Similarity	NPC100390
0.808	Intermediate Similarity	NPC254614
0.808	Intermediate Similarity	NPC478154
0.807	Intermediate Similarity	NPC474243
0.807	Intermediate Similarity	NPC42662
0.8067	Intermediate Similarity	NPC268958
0.8067	Intermediate Similarity	NPC469488
0.8053	Intermediate Similarity	NPC144854
0.8053	Intermediate Similarity	NPC3316
0.8053	Intermediate Similarity	NPC166993
0.8051	Intermediate Similarity	NPC473968
0.8051	Intermediate Similarity	NPC476713
0.8051	Intermediate Similarity	NPC469684
0.8051	Intermediate Similarity	NPC476712
0.8051	Intermediate Similarity	NPC53396
0.8051	Intermediate Similarity	NPC98249
0.8034	Intermediate Similarity	NPC470919
0.8034	Intermediate Similarity	NPC469877
0.8034	Intermediate Similarity	NPC117712
0.8017	Intermediate Similarity	NPC289312
0.8017	Intermediate Similarity	NPC472002
0.8017	Intermediate Similarity	NPC269642
0.8017	Intermediate Similarity	NPC11252
0.8017	Intermediate Similarity	NPC317687
0.8017	Intermediate Similarity	NPC473877
0.8017	Intermediate Similarity	NPC222688
0.8016	Intermediate Similarity	NPC478151
0.8	Intermediate Similarity	NPC475167
0.8	Intermediate Similarity	NPC262796
0.8	Intermediate Similarity	NPC301639
0.8	Intermediate Similarity	NPC25998
0.8	Intermediate Similarity	NPC45346
0.8	Intermediate Similarity	NPC475377
0.8	Intermediate Similarity	NPC172374
0.8	Intermediate Similarity	NPC134914
0.8	Intermediate Similarity	NPC329993
0.8	Intermediate Similarity	NPC476074
0.8	Intermediate Similarity	NPC251226
0.8	Intermediate Similarity	NPC173435
0.8	Intermediate Similarity	NPC478064
0.8	Intermediate Similarity	NPC264566
0.8	Intermediate Similarity	NPC478065
0.8	Intermediate Similarity	NPC478155
0.7984	Intermediate Similarity	NPC475636
0.7984	Intermediate Similarity	NPC295220
0.7983	Intermediate Similarity	NPC240509
0.7983	Intermediate Similarity	NPC284707
0.7982	Intermediate Similarity	NPC273155
0.7982	Intermediate Similarity	NPC192813
0.7982	Intermediate Similarity	NPC154608
0.7982	Intermediate Similarity	NPC37628
0.7982	Intermediate Similarity	NPC293850
0.7982	Intermediate Similarity	NPC277017
0.7967	Intermediate Similarity	NPC293112
0.7967	Intermediate Similarity	NPC473635
0.7967	Intermediate Similarity	NPC225049
0.7967	Intermediate Similarity	NPC87662
0.7966	Intermediate Similarity	NPC476710
0.7966	Intermediate Similarity	NPC476711
0.7966	Intermediate Similarity	NPC179626
0.7965	Intermediate Similarity	NPC200957
0.7965	Intermediate Similarity	NPC138908
0.7965	Intermediate Similarity	NPC181357
0.7951	Intermediate Similarity	NPC11895
0.7951	Intermediate Similarity	NPC472399
0.7949	Intermediate Similarity	NPC51978
0.7949	Intermediate Similarity	NPC478212
0.7949	Intermediate Similarity	NPC159333
0.7949	Intermediate Similarity	NPC471204
0.7946	Intermediate Similarity	NPC61442
0.7937	Intermediate Similarity	NPC478152
0.7937	Intermediate Similarity	NPC478153
0.7937	Intermediate Similarity	NPC478150
0.7934	Intermediate Similarity	NPC159456
0.7934	Intermediate Similarity	NPC4021
0.7934	Intermediate Similarity	NPC472000
0.7934	Intermediate Similarity	NPC471999
0.7931	Intermediate Similarity	NPC201992
0.7931	Intermediate Similarity	NPC317107
0.792	Intermediate Similarity	NPC309096
0.792	Intermediate Similarity	NPC477196
0.792	Intermediate Similarity	NPC231529
0.792	Intermediate Similarity	NPC264192
0.792	Intermediate Similarity	NPC54614
0.7917	Intermediate Similarity	NPC473839
0.7917	Intermediate Similarity	NPC472933
0.7917	Intermediate Similarity	NPC77689
0.7917	Intermediate Similarity	NPC473636
0.7917	Intermediate Similarity	NPC211093
0.7917	Intermediate Similarity	NPC230513
0.7913	Intermediate Similarity	NPC141350
0.7903	Intermediate Similarity	NPC470882
0.7899	Intermediate Similarity	NPC296822
0.7899	Intermediate Similarity	NPC478204
0.7899	Intermediate Similarity	NPC13713
0.7899	Intermediate Similarity	NPC27999
0.7899	Intermediate Similarity	NPC477116
0.7899	Intermediate Similarity	NPC134430

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 NPC190185 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	2255
0.2-0.3	3797
0.3-0.4	1712
0.4-0.5	630
0.5-0.6	250
0.6-0.7	152
0.7-0.8	60
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8468	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD6921	Approved
0.7705	Intermediate Similarity	NPD6319	Approved
0.7661	Intermediate Similarity	NPD8328	Phase 3
0.7638	Intermediate Similarity	NPD7319	Approved
0.746	Intermediate Similarity	NPD7492	Approved
0.7458	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6372	Approved
0.7458	Intermediate Similarity	NPD6373	Approved
0.7419	Intermediate Similarity	NPD6054	Approved
0.7419	Intermediate Similarity	NPD6059	Approved
0.7417	Intermediate Similarity	NPD8297	Approved
0.7402	Intermediate Similarity	NPD6616	Approved
0.7402	Intermediate Similarity	NPD7507	Approved
0.7395	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD6686	Approved
0.735	Intermediate Similarity	NPD6675	Approved
0.735	Intermediate Similarity	NPD5739	Approved
0.735	Intermediate Similarity	NPD6402	Approved
0.735	Intermediate Similarity	NPD7128	Approved
0.7344	Intermediate Similarity	NPD8293	Discontinued
0.7344	Intermediate Similarity	NPD7078	Approved
0.7333	Intermediate Similarity	NPD6649	Approved
0.7333	Intermediate Similarity	NPD6650	Approved
0.7317	Intermediate Similarity	NPD7115	Discovery
0.7302	Intermediate Similarity	NPD6370	Approved
0.7287	Intermediate Similarity	NPD7736	Approved
0.7281	Intermediate Similarity	NPD4225	Approved
0.7227	Intermediate Similarity	NPD7320	Approved
0.7227	Intermediate Similarity	NPD6881	Approved
0.7227	Intermediate Similarity	NPD6899	Approved
0.7222	Intermediate Similarity	NPD6016	Approved
0.7222	Intermediate Similarity	NPD6015	Approved
0.7213	Intermediate Similarity	NPD4632	Approved
0.7177	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5988	Approved
0.7143	Intermediate Similarity	NPD5701	Approved
0.7143	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6882	Approved
0.713	Intermediate Similarity	NPD7638	Approved
0.7107	Intermediate Similarity	NPD7290	Approved
0.7107	Intermediate Similarity	NPD6883	Approved
0.7107	Intermediate Similarity	NPD7102	Approved
0.7069	Intermediate Similarity	NPD7640	Approved
0.7069	Intermediate Similarity	NPD7639	Approved
0.7063	Intermediate Similarity	NPD7516	Approved
0.7049	Intermediate Similarity	NPD6847	Approved
0.7049	Intermediate Similarity	NPD8130	Phase 1
0.7049	Intermediate Similarity	NPD6869	Approved
0.7049	Intermediate Similarity	NPD6617	Approved
0.704	Intermediate Similarity	NPD6009	Approved
0.7025	Intermediate Similarity	NPD6012	Approved
0.7025	Intermediate Similarity	NPD6014	Approved
0.7025	Intermediate Similarity	NPD6013	Approved
0.6984	Remote Similarity	NPD7327	Approved
0.6984	Remote Similarity	NPD7328	Approved
0.6977	Remote Similarity	NPD7604	Phase 2
0.6967	Remote Similarity	NPD4634	Approved
0.6953	Remote Similarity	NPD8516	Approved
0.6953	Remote Similarity	NPD8513	Phase 3
0.6953	Remote Similarity	NPD5983	Phase 2
0.6953	Remote Similarity	NPD8517	Approved
0.6953	Remote Similarity	NPD8515	Approved
0.6942	Remote Similarity	NPD6011	Approved
0.6935	Remote Similarity	NPD8133	Approved
0.6911	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6033	Approved
0.6885	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6336	Discontinued
0.6866	Remote Similarity	NPD7260	Phase 2
0.6864	Remote Similarity	NPD1700	Approved
0.686	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5696	Approved
0.6822	Remote Similarity	NPD8335	Approved
0.6822	Remote Similarity	NPD8378	Approved
0.6822	Remote Similarity	NPD8379	Approved
0.6822	Remote Similarity	NPD8296	Approved
0.6822	Remote Similarity	NPD8380	Approved
0.6777	Remote Similarity	NPD6008	Approved
0.6752	Remote Similarity	NPD6083	Phase 2
0.6752	Remote Similarity	NPD6084	Phase 2
0.6752	Remote Similarity	NPD4755	Approved
0.6744	Remote Similarity	NPD8377	Approved
0.6744	Remote Similarity	NPD8294	Approved
0.6721	Remote Similarity	NPD6412	Phase 2
0.6694	Remote Similarity	NPD6371	Approved
0.6693	Remote Similarity	NPD6274	Approved
0.6692	Remote Similarity	NPD8074	Phase 3
0.6692	Remote Similarity	NPD8033	Approved
0.6691	Remote Similarity	NPD6845	Suspended
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD7101	Approved
0.664	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4696	Approved
0.6639	Remote Similarity	NPD4700	Approved
0.6639	Remote Similarity	NPD5285	Approved
0.6639	Remote Similarity	NPD5286	Approved
0.6619	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7902	Approved
0.6589	Remote Similarity	NPD6335	Approved
0.6583	Remote Similarity	NPD5344	Discontinued
0.6565	Remote Similarity	NPD6908	Approved
0.6565	Remote Similarity	NPD7503	Approved
0.6565	Remote Similarity	NPD6909	Approved
0.6557	Remote Similarity	NPD5141	Approved
0.6529	Remote Similarity	NPD5224	Approved
0.6529	Remote Similarity	NPD5225	Approved
0.6529	Remote Similarity	NPD5226	Approved
0.6529	Remote Similarity	NPD4633	Approved
0.6529	Remote Similarity	NPD7632	Discontinued
0.6525	Remote Similarity	NPD4697	Phase 3
0.6512	Remote Similarity	NPD6317	Approved
0.6504	Remote Similarity	NPD4767	Approved
0.6504	Remote Similarity	NPD4768	Approved
0.6496	Remote Similarity	NPD7748	Approved
0.6496	Remote Similarity	NPD5282	Discontinued
0.6475	Remote Similarity	NPD5175	Approved
0.6475	Remote Similarity	NPD5174	Approved
0.6466	Remote Similarity	NPD7515	Phase 2
0.6462	Remote Similarity	NPD6314	Approved
0.6462	Remote Similarity	NPD6313	Approved
0.6457	Remote Similarity	NPD6053	Discontinued
0.6446	Remote Similarity	NPD5223	Approved
0.6441	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5695	Phase 3
0.6439	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5328	Approved
0.6434	Remote Similarity	NPD6868	Approved
0.6423	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6399	Phase 3
0.64	Remote Similarity	NPD4730	Approved
0.64	Remote Similarity	NPD4729	Approved
0.6387	Remote Similarity	NPD5222	Approved
0.6387	Remote Similarity	NPD5221	Approved
0.6387	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7900	Approved
0.6356	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6672	Approved
0.6348	Remote Similarity	NPD5737	Approved
0.6341	Remote Similarity	NPD4754	Approved
0.6333	Remote Similarity	NPD5173	Approved
0.6325	Remote Similarity	NPD5693	Phase 1
0.6325	Remote Similarity	NPD6411	Approved
0.6325	Remote Similarity	NPD8035	Phase 2
0.6325	Remote Similarity	NPD8034	Phase 2
0.6325	Remote Similarity	NPD6079	Approved
0.6325	Remote Similarity	NPD7983	Approved
0.6316	Remote Similarity	NPD3618	Phase 1
0.6312	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4629	Approved
0.6303	Remote Similarity	NPD5210	Approved
0.6299	Remote Similarity	NPD5248	Approved
0.6299	Remote Similarity	NPD5249	Phase 3
0.6299	Remote Similarity	NPD5247	Approved
0.6299	Remote Similarity	NPD5250	Approved
0.6299	Remote Similarity	NPD5251	Approved
0.6271	Remote Similarity	NPD5778	Approved
0.6271	Remote Similarity	NPD5779	Approved
0.627	Remote Similarity	NPD5128	Approved
0.6261	Remote Similarity	NPD3573	Approved
0.6241	Remote Similarity	NPD8415	Approved
0.623	Remote Similarity	NPD6648	Approved
0.6228	Remote Similarity	NPD1694	Approved
0.6187	Remote Similarity	NPD5956	Approved
0.6182	Remote Similarity	NPD6114	Approved
0.6182	Remote Similarity	NPD6697	Approved
0.6182	Remote Similarity	NPD6115	Approved
0.6182	Remote Similarity	NPD6118	Approved
0.6168	Remote Similarity	NPD8407	Phase 2
0.6167	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6101	Approved
0.6154	Remote Similarity	NPD6904	Approved
0.6154	Remote Similarity	NPD6673	Approved
0.6154	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4753	Phase 2
0.6154	Remote Similarity	NPD6080	Approved
0.6134	Remote Similarity	NPD4202	Approved
0.6124	Remote Similarity	NPD5217	Approved
0.6124	Remote Similarity	NPD5216	Approved
0.6124	Remote Similarity	NPD5215	Approved
0.6111	Remote Similarity	NPD6334	Approved
0.6111	Remote Similarity	NPD6333	Approved
0.6106	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD6067	Discontinued
0.6095	Remote Similarity	NPD8434	Phase 2
0.6091	Remote Similarity	NPD6116	Phase 1
0.6087	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD8368	Discontinued
0.6055	Remote Similarity	NPD3703	Phase 2
0.605	Remote Similarity	NPD7637	Suspended
0.6047	Remote Similarity	NPD5135	Approved
0.6047	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD5169	Approved
0.6037	Remote Similarity	NPD7799	Discontinued
0.6034	Remote Similarity	NPD5330	Approved
0.6034	Remote Similarity	NPD7521	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