NPASS Compound

Structure

CID112038 OpenBabel06191715462D 29 33 0 0 1 0 0 0 0 0999 V2000 -2.9345 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1748 0.0242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 0.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2613 0.4310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 2.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8005 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 2.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2880 -0.0346 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9345 1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8040 1.5425 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8495 2.2280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0685 1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2398 1.1507 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6665 1.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0364 -1.0025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 0.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 1.0500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7772 2.6012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1478 0.1550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8918 -0.3369 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 0.3419 2.6909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 2 0 0 0 0 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 9 1 0 0 0 0 5 11 1 0 0 0 0 6 18 1 0 0 0 0 6 28 1 0 0 0 0 7 9 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 0 0 0 0 9 17 1 6 0 0 0 10 13 1 0 0 0 0 10 21 2 0 0 0 0 11 18 1 1 0 0 0 11 29 1 0 0 0 0 12 20 1 1 0 0 0 12 22 1 0 0 0 0 13 17 1 6 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 6 0 0 0 14 24 1 0 0 0 0 15 25 2 0 0 0 0 15 29 1 0 0 0 0 16 17 1 6 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 3 1 6 0 0 0 18 19 1 1 0 0 0 19 26 1 6 0 0 0 20 27 1 1 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.14
Volume:	380.26
LogP:	0.703
LogD:	-0.146
LogS:	-3.648
# Rotatable Bonds:	0
TPSA:	150.59
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.212
Synthetic Accessibility Score:	6.863
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.658
MDCK Permeability:	5.480931940837763e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.147
20% Bioavailability (F20%):	0.855
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.361
Plasma Protein Binding (PPB):	49.139957427978516%
Volume Distribution (VD):	0.397
Pgp-substrate:	64.8676528930664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.901
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.325
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	1.738
Half-life (T1/2):	0.148

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.221
Drug-inuced Liver Injury (DILI):	0.269
AMES Toxicity:	0.107
Rat Oral Acute Toxicity:	0.698
Maximum Recommended Daily Dose:	0.706
Skin Sensitization:	0.326
Carcinogencity:	0.081
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC112038

Natural Product ID:	NPC112038
*Common Name:**	Eurycomanone
IUPAC Name:	n.a.
Synonyms:	Eurycomanone
Standard InCHIKey:	UCUWZJWAQQRCOR-AIMGAIMTSA-N
Standard InCHI:	InChI=1S/C20H24O9/c1-7-4-10(21)13(23)17(3)9(7)5-11-18-6-28-20(27,16(17)18)12(22)8(2)19(18,26)14(24)15(25)29-11/h4,9,11-14,16,22-24,26-27H,2,5-6H2,1,3H3/t9-,11+,12+,13+,14-,16+,17+,18+,19-,20+/m0/s1
SMILES:	CC1=CC(=O)[C@H]([C@]2([C@H]1C[C@H]1OC(=O)[C@@H]([C@@]3([C@]41[C@@H]2[C@](O)(OC4)[C@@H](C3=C)O)O)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1171981
PubChem CID:	49798945
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[14575431]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	root	n.a.	PMID[1800638]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919052]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24467387]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[25066952]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	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
ED50	8
IC50	4
LD50	2
Others	7

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	6
Organism	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.9	ug ml-1	PMID[507661]
NPT168	Cell Line	P388	Mus musculus	ED50	>	20.0	ug ml-1	PMID[507661]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	96.78	%	PMID[507664]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	101.4	%	PMID[507664]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	87.22	%	PMID[507664]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	100.9	%	PMID[507664]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	97.47	%	PMID[507664]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	47.03	%	PMID[507664]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.8	ug ml-1	PMID[507661]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.2	ug ml-1	PMID[507661]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	8.2	ug ml-1	PMID[507661]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	14.3	ug ml-1	PMID[507661]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.1	ug ml-1	PMID[507661]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.2	ug ml-1	PMID[507661]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.0477	ug.mL-1	PMID[507661]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.0481	ug.mL-1	PMID[507661]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.04	ug.mL-1	PMID[507662]
NPT140	Organism	Artemia	Artemia	LD50	=	3.5	ug ml-1	PMID[507663]
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	0.05	g/Kg	PMID[507663]
NPT2	Others	Unspecified		IC50	=	2400.0	nM	PMID[507663]
NPT2	Others	Unspecified		Inhibition	>	50.0	%	PMID[507663]

☑ 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 NPC112038 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	252
0.1-0.2	1493
0.2-0.3	4236
0.3-0.4	7298
0.4-0.5	11328
0.5-0.6	8510
0.6-0.7	5422
0.7-0.8	3556
0.8-0.85	467
0.85-0.9	64
0.9-0.95	57
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9818	High Similarity	NPC188667
0.9818	High Similarity	NPC204552
0.9558	High Similarity	NPC102822
0.9558	High Similarity	NPC477046
0.9554	High Similarity	NPC469488
0.955	High Similarity	NPC470854
0.955	High Similarity	NPC287343
0.955	High Similarity	NPC474654
0.955	High Similarity	NPC97908
0.955	High Similarity	NPC122033
0.9464	High Similarity	NPC297179
0.9464	High Similarity	NPC251310
0.9455	High Similarity	NPC208998
0.9455	High Similarity	NPC51978
0.9455	High Similarity	NPC7921
0.9375	High Similarity	NPC176513
0.9375	High Similarity	NPC470775
0.9364	High Similarity	NPC11252
0.9364	High Similarity	NPC289312
0.931	High Similarity	NPC470922
0.9292	High Similarity	NPC17772
0.9286	High Similarity	NPC235539
0.9286	High Similarity	NPC134869
0.9286	High Similarity	NPC152199
0.9279	High Similarity	NPC49451
0.9273	High Similarity	NPC201992
0.9273	High Similarity	NPC146945
0.9273	High Similarity	NPC171888
0.9196	High Similarity	NPC18547
0.9196	High Similarity	NPC474906
0.9189	High Similarity	NPC302146
0.9123	High Similarity	NPC470776
0.9115	High Similarity	NPC474046
0.9115	High Similarity	NPC251236
0.9115	High Similarity	NPC470628
0.9115	High Similarity	NPC96312
0.9115	High Similarity	NPC259306
0.9115	High Similarity	NPC40632
0.9115	High Similarity	NPC328374
0.906	High Similarity	NPC67251
0.9043	High Similarity	NPC475775
0.9043	High Similarity	NPC476529
0.9043	High Similarity	NPC470777
0.9027	High Similarity	NPC470919
0.9027	High Similarity	NPC473798
0.9027	High Similarity	NPC469877
0.9018	High Similarity	NPC474516
0.9	High Similarity	NPC293850
0.8983	High Similarity	NPC24651
0.8983	High Similarity	NPC476729
0.8974	High Similarity	NPC312833
0.8966	High Similarity	NPC107338
0.8966	High Similarity	NPC109607
0.8947	High Similarity	NPC207217
0.8947	High Similarity	NPC474734
0.8919	High Similarity	NPC472534
0.8919	High Similarity	NPC143706
0.8908	High Similarity	NPC225049
0.8898	High Similarity	NPC91693
0.8898	High Similarity	NPC265557
0.8898	High Similarity	NPC105926
0.8898	High Similarity	NPC18945
0.887	High Similarity	NPC27999
0.887	High Similarity	NPC473968
0.887	High Similarity	NPC477116
0.886	High Similarity	NPC143268
0.886	High Similarity	NPC268238
0.886	High Similarity	NPC45218
0.886	High Similarity	NPC323821
0.885	High Similarity	NPC472002
0.8833	High Similarity	NPC470780
0.8783	High Similarity	NPC173686
0.8783	High Similarity	NPC179626
0.8783	High Similarity	NPC16081
0.8739	High Similarity	NPC3316
0.8739	High Similarity	NPC144854
0.8729	High Similarity	NPC470779
0.8718	High Similarity	NPC268958
0.8707	High Similarity	NPC473590
0.8707	High Similarity	NPC309433
0.8699	High Similarity	NPC102316
0.8696	High Similarity	NPC117712
0.8696	High Similarity	NPC243354
0.8673	High Similarity	NPC474567
0.8661	High Similarity	NPC154608
0.8661	High Similarity	NPC192813
0.8661	High Similarity	NPC277017
0.8655	High Similarity	NPC222688
0.8629	High Similarity	NPC168879
0.8609	High Similarity	NPC194273
0.8607	High Similarity	NPC188291
0.8596	High Similarity	NPC471243
0.8584	High Similarity	NPC141350
0.8571	High Similarity	NPC251998
0.8571	High Similarity	NPC243014
0.8548	High Similarity	NPC100390
0.8548	High Similarity	NPC254614
0.8547	High Similarity	NPC470171
0.8525	High Similarity	NPC470882
0.8525	High Similarity	NPC476008
0.8504	High Similarity	NPC140045
0.8504	High Similarity	NPC596
0.8504	High Similarity	NPC295885
0.8492	Intermediate Similarity	NPC262813
0.8482	Intermediate Similarity	NPC102352
0.8455	Intermediate Similarity	NPC475636
0.8455	Intermediate Similarity	NPC295220
0.8448	Intermediate Similarity	NPC320118
0.8448	Intermediate Similarity	NPC194100
0.8443	Intermediate Similarity	NPC87662
0.8443	Intermediate Similarity	NPC285091
0.8443	Intermediate Similarity	NPC477745
0.8435	Intermediate Similarity	NPC157476
0.843	Intermediate Similarity	NPC227397
0.8425	Intermediate Similarity	NPC471089
0.8425	Intermediate Similarity	NPC141215
0.8425	Intermediate Similarity	NPC190065
0.8413	Intermediate Similarity	NPC15215
0.8413	Intermediate Similarity	NPC242486
0.8407	Intermediate Similarity	NPC230541
0.8403	Intermediate Similarity	NPC122971
0.84	Intermediate Similarity	NPC254146
0.84	Intermediate Similarity	NPC33378
0.84	Intermediate Similarity	NPC6274
0.8393	Intermediate Similarity	NPC475036
0.839	Intermediate Similarity	NPC470778
0.839	Intermediate Similarity	NPC469684
0.839	Intermediate Similarity	NPC146432
0.839	Intermediate Similarity	NPC218970
0.8387	Intermediate Similarity	NPC309096
0.8387	Intermediate Similarity	NPC476851
0.8387	Intermediate Similarity	NPC54614
0.8387	Intermediate Similarity	NPC264192
0.8376	Intermediate Similarity	NPC247069
0.8376	Intermediate Similarity	NPC299849
0.8374	Intermediate Similarity	NPC473265
0.8362	Intermediate Similarity	NPC90769
0.8362	Intermediate Similarity	NPC269530
0.8362	Intermediate Similarity	NPC174836
0.8362	Intermediate Similarity	NPC473397
0.8361	Intermediate Similarity	NPC473255
0.8348	Intermediate Similarity	NPC85391
0.8348	Intermediate Similarity	NPC210005
0.8347	Intermediate Similarity	NPC269642
0.8347	Intermediate Similarity	NPC471965
0.8333	Intermediate Similarity	NPC478151
0.8333	Intermediate Similarity	NPC472004
0.832	Intermediate Similarity	NPC476074
0.832	Intermediate Similarity	NPC475377
0.832	Intermediate Similarity	NPC478065
0.832	Intermediate Similarity	NPC45346
0.832	Intermediate Similarity	NPC172374
0.832	Intermediate Similarity	NPC476852
0.832	Intermediate Similarity	NPC475167
0.832	Intermediate Similarity	NPC134914
0.832	Intermediate Similarity	NPC262796
0.832	Intermediate Similarity	NPC173435
0.832	Intermediate Similarity	NPC478064
0.832	Intermediate Similarity	NPC264566
0.832	Intermediate Similarity	NPC329993
0.832	Intermediate Similarity	NPC301639
0.8319	Intermediate Similarity	NPC181357
0.8306	Intermediate Similarity	NPC476859
0.8306	Intermediate Similarity	NPC311534
0.8305	Intermediate Similarity	NPC213084
0.8305	Intermediate Similarity	NPC190185
0.8305	Intermediate Similarity	NPC89929
0.8293	Intermediate Similarity	NPC47113
0.8293	Intermediate Similarity	NPC181999
0.8293	Intermediate Similarity	NPC293112
0.8293	Intermediate Similarity	NPC174367
0.8291	Intermediate Similarity	NPC471252
0.8291	Intermediate Similarity	NPC94509
0.8291	Intermediate Similarity	NPC255017
0.8291	Intermediate Similarity	NPC198539
0.8291	Intermediate Similarity	NPC477266
0.8279	Intermediate Similarity	NPC471964
0.8279	Intermediate Similarity	NPC262199
0.8279	Intermediate Similarity	NPC478066
0.8279	Intermediate Similarity	NPC202666
0.8279	Intermediate Similarity	NPC471961
0.8279	Intermediate Similarity	NPC14617
0.8276	Intermediate Similarity	NPC188738
0.8276	Intermediate Similarity	NPC29505
0.8276	Intermediate Similarity	NPC213320
0.8264	Intermediate Similarity	NPC472401
0.8264	Intermediate Similarity	NPC202051
0.8264	Intermediate Similarity	NPC275675
0.8264	Intermediate Similarity	NPC75417
0.8261	Intermediate Similarity	NPC218853
0.8254	Intermediate Similarity	NPC478153
0.8254	Intermediate Similarity	NPC471855
0.8254	Intermediate Similarity	NPC478154
0.8254	Intermediate Similarity	NPC478152
0.8254	Intermediate Similarity	NPC478150
0.825	Intermediate Similarity	NPC319570
0.825	Intermediate Similarity	NPC77689
0.825	Intermediate Similarity	NPC473636
0.824	Intermediate Similarity	NPC231529
0.824	Intermediate Similarity	NPC470880

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 NPC112038 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	1684
0.2-0.3	3815
0.3-0.4	2162
0.4-0.5	687
0.5-0.6	316
0.6-0.7	153
0.7-0.8	113
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8279	Intermediate Similarity	NPD8328	Phase 3
0.8182	Intermediate Similarity	NPD6319	Approved
0.8174	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD7492	Approved
0.8033	Intermediate Similarity	NPD6059	Approved
0.8033	Intermediate Similarity	NPD6054	Approved
0.8016	Intermediate Similarity	NPD7736	Approved
0.8	Intermediate Similarity	NPD6616	Approved
0.7967	Intermediate Similarity	NPD6016	Approved
0.7967	Intermediate Similarity	NPD6015	Approved
0.7953	Intermediate Similarity	NPD7319	Approved
0.7937	Intermediate Similarity	NPD8293	Discontinued
0.7937	Intermediate Similarity	NPD7078	Approved
0.7934	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD5988	Approved
0.7903	Intermediate Similarity	NPD6370	Approved
0.7833	Intermediate Similarity	NPD4632	Approved
0.7797	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD6009	Approved
0.775	Intermediate Similarity	NPD8297	Approved
0.775	Intermediate Similarity	NPD6882	Approved
0.7717	Intermediate Similarity	NPD7507	Approved
0.7692	Intermediate Similarity	NPD6675	Approved
0.7692	Intermediate Similarity	NPD6402	Approved
0.7692	Intermediate Similarity	NPD7128	Approved
0.7692	Intermediate Similarity	NPD5739	Approved
0.7647	Intermediate Similarity	NPD6372	Approved
0.7647	Intermediate Similarity	NPD6373	Approved
0.7647	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7115	Discovery
0.7627	Intermediate Similarity	NPD5701	Approved
0.7627	Intermediate Similarity	NPD6412	Phase 2
0.7627	Intermediate Similarity	NPD5697	Approved
0.7583	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD4634	Approved
0.7563	Intermediate Similarity	NPD7320	Approved
0.7563	Intermediate Similarity	NPD6899	Approved
0.7563	Intermediate Similarity	NPD6686	Approved
0.7563	Intermediate Similarity	NPD6881	Approved
0.754	Intermediate Similarity	NPD8513	Phase 3
0.754	Intermediate Similarity	NPD8517	Approved
0.754	Intermediate Similarity	NPD6921	Approved
0.754	Intermediate Similarity	NPD8516	Approved
0.754	Intermediate Similarity	NPD8515	Approved
0.7521	Intermediate Similarity	NPD6650	Approved
0.7521	Intermediate Similarity	NPD6649	Approved
0.752	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.7478	Intermediate Similarity	NPD4225	Approved
0.7462	Intermediate Similarity	NPD6033	Approved
0.744	Intermediate Similarity	NPD7328	Approved
0.744	Intermediate Similarity	NPD7327	Approved
0.7438	Intermediate Similarity	NPD6883	Approved
0.7438	Intermediate Similarity	NPD7290	Approved
0.7438	Intermediate Similarity	NPD7102	Approved
0.7436	Intermediate Similarity	NPD5211	Phase 2
0.7417	Intermediate Similarity	NPD6011	Approved
0.7402	Intermediate Similarity	NPD5983	Phase 2
0.7395	Intermediate Similarity	NPD6008	Approved
0.7391	Intermediate Similarity	NPD4755	Approved
0.7377	Intermediate Similarity	NPD6617	Approved
0.7377	Intermediate Similarity	NPD6869	Approved
0.7377	Intermediate Similarity	NPD6847	Approved
0.7377	Intermediate Similarity	NPD8130	Phase 1
0.7333	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5141	Approved
0.7287	Intermediate Similarity	NPD7604	Phase 2
0.7265	Intermediate Similarity	NPD5286	Approved
0.7265	Intermediate Similarity	NPD4700	Approved
0.7265	Intermediate Similarity	NPD4696	Approved
0.7265	Intermediate Similarity	NPD5285	Approved
0.7236	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6336	Discontinued
0.7143	Intermediate Similarity	NPD5225	Approved
0.7143	Intermediate Similarity	NPD5226	Approved
0.7143	Intermediate Similarity	NPD4633	Approved
0.7143	Intermediate Similarity	NPD5224	Approved
0.7143	Intermediate Similarity	NPD6274	Approved
0.7132	Intermediate Similarity	NPD8033	Approved
0.7132	Intermediate Similarity	NPD8379	Approved
0.7132	Intermediate Similarity	NPD8296	Approved
0.7132	Intermediate Similarity	NPD8378	Approved
0.7132	Intermediate Similarity	NPD8380	Approved
0.7132	Intermediate Similarity	NPD8335	Approved
0.713	Intermediate Similarity	NPD7748	Approved
0.7121	Intermediate Similarity	NPD8074	Phase 3
0.712	Intermediate Similarity	NPD8133	Approved
0.7119	Intermediate Similarity	NPD7640	Approved
0.7119	Intermediate Similarity	NPD7639	Approved
0.7107	Intermediate Similarity	NPD4767	Approved
0.7107	Intermediate Similarity	NPD4768	Approved
0.7105	Intermediate Similarity	NPD7515	Phase 2
0.7097	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6084	Phase 2
0.7094	Intermediate Similarity	NPD6083	Phase 2
0.7094	Intermediate Similarity	NPD7902	Approved
0.7083	Intermediate Similarity	NPD5175	Approved
0.7083	Intermediate Similarity	NPD5174	Approved
0.7059	Intermediate Similarity	NPD5223	Approved
0.7054	Intermediate Similarity	NPD3573	Approved
0.7054	Intermediate Similarity	NPD8294	Approved
0.7054	Intermediate Similarity	NPD8377	Approved
0.7034	Intermediate Similarity	NPD7638	Approved
0.7009	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4697	Phase 3
0.7009	Intermediate Similarity	NPD5222	Approved
0.7009	Intermediate Similarity	NPD5221	Approved
0.7	Intermediate Similarity	NPD7503	Approved
0.6992	Remote Similarity	NPD4730	Approved
0.6992	Remote Similarity	NPD4729	Approved
0.6983	Remote Similarity	NPD5282	Discontinued
0.6977	Remote Similarity	NPD7100	Approved
0.6977	Remote Similarity	NPD7101	Approved
0.6957	Remote Similarity	NPD6411	Approved
0.6953	Remote Similarity	NPD6317	Approved
0.6949	Remote Similarity	NPD5173	Approved
0.6942	Remote Similarity	NPD4754	Approved
0.693	Remote Similarity	NPD5328	Approved
0.6923	Remote Similarity	NPD5695	Phase 3
0.6917	Remote Similarity	NPD5344	Discontinued
0.6899	Remote Similarity	NPD6335	Approved
0.6899	Remote Similarity	NPD6314	Approved
0.6899	Remote Similarity	NPD6313	Approved
0.6897	Remote Similarity	NPD5779	Approved
0.6897	Remote Similarity	NPD5778	Approved
0.6897	Remote Similarity	NPD6399	Phase 3
0.6891	Remote Similarity	NPD5696	Approved
0.688	Remote Similarity	NPD5250	Approved
0.688	Remote Similarity	NPD5251	Approved
0.688	Remote Similarity	NPD5248	Approved
0.688	Remote Similarity	NPD5249	Phase 3
0.688	Remote Similarity	NPD5247	Approved
0.687	Remote Similarity	NPD6908	Approved
0.687	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6909	Approved
0.6855	Remote Similarity	NPD5128	Approved
0.6838	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7900	Approved
0.6838	Remote Similarity	NPD5956	Approved
0.6814	Remote Similarity	NPD3618	Phase 1
0.681	Remote Similarity	NPD7983	Approved
0.681	Remote Similarity	NPD6079	Approved
0.6783	Remote Similarity	NPD4753	Phase 2
0.6783	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6101	Approved
0.6774	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD6067	Discontinued
0.6752	Remote Similarity	NPD4202	Approved
0.6746	Remote Similarity	NPD6371	Approved
0.6744	Remote Similarity	NPD6868	Approved
0.6724	Remote Similarity	NPD46	Approved
0.6724	Remote Similarity	NPD6698	Approved
0.6696	Remote Similarity	NPD5737	Approved
0.6696	Remote Similarity	NPD6672	Approved
0.6693	Remote Similarity	NPD5217	Approved
0.6693	Remote Similarity	NPD5215	Approved
0.6693	Remote Similarity	NPD5216	Approved
0.6667	Remote Similarity	NPD7260	Phase 2
0.6641	Remote Similarity	NPD6053	Discontinued
0.6639	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5135	Approved
0.6614	Remote Similarity	NPD5169	Approved
0.6607	Remote Similarity	NPD3667	Approved
0.6585	Remote Similarity	NPD7632	Discontinued
0.6562	Remote Similarity	NPD5127	Approved
0.6557	Remote Similarity	NPD6648	Approved
0.6552	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7637	Suspended
0.6525	Remote Similarity	NPD5693	Phase 1
0.6522	Remote Similarity	NPD7521	Approved
0.6522	Remote Similarity	NPD5330	Approved
0.6522	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD7334	Approved
0.6522	Remote Similarity	NPD6684	Approved
0.6522	Remote Similarity	NPD6409	Approved
0.6504	Remote Similarity	NPD1700	Approved
0.6503	Remote Similarity	NPD6333	Approved
0.6503	Remote Similarity	NPD6334	Approved
0.65	Remote Similarity	NPD6845	Suspended
0.65	Remote Similarity	NPD5210	Approved
0.65	Remote Similarity	NPD4629	Approved
0.65	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6080	Approved
0.6496	Remote Similarity	NPD6673	Approved
0.6496	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6904	Approved
0.6491	Remote Similarity	NPD3666	Approved
0.6491	Remote Similarity	NPD3665	Phase 1
0.6491	Remote Similarity	NPD4786	Approved
0.6491	Remote Similarity	NPD3133	Approved
0.648	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7524	Approved
0.6466	Remote Similarity	NPD4522	Approved
0.6457	Remote Similarity	NPD5168	Approved
0.6446	Remote Similarity	NPD7839	Suspended

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