NPASS Compound

Structure

NPC261992 OpenBabel07101718292D 35 36 0 0 1 0 0 0 0 0999 V2000 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6962 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 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 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 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 0.8660 0.5000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 14 2 0 0 0 0 11 23 1 0 0 0 0 12 13 2 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 24 2 0 0 0 0 17 27 1 0 0 0 0 18 23 2 0 0 0 0 18 28 1 0 0 0 0 19 23 1 0 0 0 0 19 31 1 0 0 0 0 20 24 1 0 0 0 0 20 35 1 0 0 0 0 25 27 2 0 0 0 0 25 29 1 0 0 0 0 26 28 2 0 0 0 0 26 30 1 0 0 0 0 27 32 1 0 0 0 0 28 35 1 0 0 0 0 29 5 1 1 0 0 0 29 33 1 0 0 0 0 30 6 1 6 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	538.455
LogP:	5.945
LogD:	4.413
LogS:	-3.818
# Rotatable Bonds:	14
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.244
Synthetic Accessibility Score:	3.591
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.641
MDCK Permeability:	1.749328112055082e-05
Pgp-inhibitor:	0.803
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.604
30% Bioavailability (F30%):	0.476

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.412
Plasma Protein Binding (PPB):	96.96666717529297%
Volume Distribution (VD):	3.54
Pgp-substrate:	3.722943067550659%

ADMET: Metabolism

CYP1A2-inhibitor:	0.162
CYP1A2-substrate:	0.212
CYP2C19-inhibitor:	0.625
CYP2C19-substrate:	0.868
CYP2C9-inhibitor:	0.458
CYP2C9-substrate:	0.864
CYP2D6-inhibitor:	0.871
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.906
CYP3A4-substrate:	0.868

ADMET: Excretion

Clearance (CL):	11.679
Half-life (T1/2):	0.139

ADMET: Toxicity

hERG Blockers:	0.272
Human Hepatotoxicity (H-HT):	0.072
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.136
Skin Sensitization:	0.177
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC261992

Natural Product ID:	NPC261992
*Common Name:**	Disydonol A
IUPAC Name:	2-[(2S)-2-hydroxy-6-methylheptan-2-yl]-5-[[5-(hydroxymethyl)-2-[(2S)-2-hydroxy-6-methylheptan-2-yl]phenoxy]methyl]phenol
Synonyms:	Disydonol A
Standard InCHIKey:	UNABCQHOHCCBEK-KYJUHHDHSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-21(2)9-7-15-29(5,33)25-13-12-24(17-27(25)32)20-35-28-18-23(19-31)11-14-26(28)30(6,34)16-8-10-22(3)4/h11-14,17-18,21-22,31-34H,7-10,15-16,19-20H2,1-6H3/t29-,30-/m0/s1
SMILES:	OCc1ccc(c(c1)OCc1ccc(c(c1)O)[C@](CCCC(C)C)(O)C)[C@](CCCC(C)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1946640
PubChem CID:	57334110
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	rhizosphere	Sonoran desert	n.a.	PMID[15620238]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17542490]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17564467]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053517]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21366228]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	healthy leaf of Ginkgo biloba	campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	isolated from the sponge Xestospongia testudinaria	n.a.	n.a.	PMID[22225637]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	Isolated from a sandy-loam soil sample	50 m inland from Waikiki Beach, Honolulu, Hawaii	2010-JUL	PMID[22400916]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22703109]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23527875]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24050204]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25001296]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25581396]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26273902]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31012585]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33305943]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	9.31	ug.mL-1	PMID[529683]
NPT2306	Cell Line	Ca-Ski	Homo sapiens	IC50	=	12.4	ug.mL-1	PMID[529683]

☑ 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 NPC261992 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	320
0.1-0.2	1359
0.2-0.3	3521
0.3-0.4	11036
0.4-0.5	8092
0.5-0.6	4705
0.6-0.7	9661
0.7-0.8	3461
0.8-0.85	477
0.85-0.9	62
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9914	High Similarity	NPC188997
0.92	High Similarity	NPC472590
0.8966	High Similarity	NPC228452
0.8934	High Similarity	NPC77789
0.8934	High Similarity	NPC18128
0.8898	High Similarity	NPC301321
0.8889	High Similarity	NPC472797
0.8871	High Similarity	NPC131397
0.8871	High Similarity	NPC476254
0.8843	High Similarity	NPC474131
0.8833	High Similarity	NPC283616
0.881	High Similarity	NPC38604
0.881	High Similarity	NPC211179
0.876	High Similarity	NPC471449
0.876	High Similarity	NPC469610
0.876	High Similarity	NPC51341
0.876	High Similarity	NPC32152
0.874	High Similarity	NPC472795
0.874	High Similarity	NPC472796
0.8702	High Similarity	NPC472800
0.8699	High Similarity	NPC48623
0.8699	High Similarity	NPC168707
0.8699	High Similarity	NPC212965
0.8689	High Similarity	NPC232295
0.8682	High Similarity	NPC469611
0.8678	High Similarity	NPC190514
0.8651	High Similarity	NPC283049
0.8651	High Similarity	NPC230479
0.8651	High Similarity	NPC26879
0.8651	High Similarity	NPC50315
0.864	High Similarity	NPC61685
0.8629	High Similarity	NPC204535
0.8629	High Similarity	NPC120638
0.8629	High Similarity	NPC46586
0.8618	High Similarity	NPC218753
0.8618	High Similarity	NPC96423
0.8618	High Similarity	NPC45663
0.8615	High Similarity	NPC211352
0.8607	High Similarity	NPC184302
0.8607	High Similarity	NPC151197
0.8605	High Similarity	NPC153019
0.8605	High Similarity	NPC8899
0.8595	High Similarity	NPC187993
0.8595	High Similarity	NPC238176
0.8594	High Similarity	NPC93962
0.8594	High Similarity	NPC96719
0.8594	High Similarity	NPC222108
0.8583	High Similarity	NPC473221
0.8583	High Similarity	NPC46978
0.8583	High Similarity	NPC232165
0.8571	High Similarity	NPC81641
0.8561	High Similarity	NPC327735
0.8561	High Similarity	NPC126101
0.856	High Similarity	NPC474130
0.856	High Similarity	NPC96940
0.8538	High Similarity	NPC472798
0.8534	High Similarity	NPC66834
0.8525	High Similarity	NPC63010
0.8516	High Similarity	NPC38664
0.8516	High Similarity	NPC53986
0.8512	High Similarity	NPC69539
0.8504	High Similarity	NPC82299
0.85	High Similarity	NPC470837
0.8492	Intermediate Similarity	NPC248557
0.8492	Intermediate Similarity	NPC270030
0.8487	Intermediate Similarity	NPC474920
0.8468	Intermediate Similarity	NPC100108
0.8468	Intermediate Similarity	NPC129176
0.8468	Intermediate Similarity	NPC277798
0.8462	Intermediate Similarity	NPC211413
0.8462	Intermediate Similarity	NPC68205
0.8462	Intermediate Similarity	NPC244888
0.8462	Intermediate Similarity	NPC164804
0.8462	Intermediate Similarity	NPC293203
0.8462	Intermediate Similarity	NPC118683
0.8455	Intermediate Similarity	NPC121866
0.8455	Intermediate Similarity	NPC137294
0.8455	Intermediate Similarity	NPC85895
0.845	Intermediate Similarity	NPC16577
0.8443	Intermediate Similarity	NPC470759
0.8443	Intermediate Similarity	NPC15860
0.8443	Intermediate Similarity	NPC219070
0.8443	Intermediate Similarity	NPC69261
0.8443	Intermediate Similarity	NPC33270
0.8443	Intermediate Similarity	NPC127894
0.8438	Intermediate Similarity	NPC66331
0.8433	Intermediate Similarity	NPC183781
0.843	Intermediate Similarity	NPC808
0.843	Intermediate Similarity	NPC473718
0.8425	Intermediate Similarity	NPC4286
0.8425	Intermediate Similarity	NPC76119
0.8421	Intermediate Similarity	NPC141717
0.8421	Intermediate Similarity	NPC476698
0.8413	Intermediate Similarity	NPC474160
0.8413	Intermediate Similarity	NPC280704
0.8409	Intermediate Similarity	NPC478085
0.8397	Intermediate Similarity	NPC27578
0.8397	Intermediate Similarity	NPC13005
0.8397	Intermediate Similarity	NPC289624
0.8387	Intermediate Similarity	NPC328485
0.8385	Intermediate Similarity	NPC475880
0.8374	Intermediate Similarity	NPC139047
0.8374	Intermediate Similarity	NPC9592
0.8374	Intermediate Similarity	NPC48781
0.8372	Intermediate Similarity	NPC39064
0.8372	Intermediate Similarity	NPC274717
0.8372	Intermediate Similarity	NPC47288
0.8372	Intermediate Similarity	NPC47283
0.8361	Intermediate Similarity	NPC290470
0.8361	Intermediate Similarity	NPC154256
0.8361	Intermediate Similarity	NPC150624
0.8361	Intermediate Similarity	NPC114064
0.8358	Intermediate Similarity	NPC134260
0.8333	Intermediate Similarity	NPC269528
0.8333	Intermediate Similarity	NPC150026
0.8333	Intermediate Similarity	NPC26394
0.8333	Intermediate Similarity	NPC77196
0.8333	Intermediate Similarity	NPC85488
0.8333	Intermediate Similarity	NPC302211
0.8321	Intermediate Similarity	NPC160623
0.8321	Intermediate Similarity	NPC280653
0.8321	Intermediate Similarity	NPC477616
0.8321	Intermediate Similarity	NPC164574
0.8321	Intermediate Similarity	NPC118114
0.8321	Intermediate Similarity	NPC228369
0.8321	Intermediate Similarity	NPC300875
0.8321	Intermediate Similarity	NPC196765
0.8321	Intermediate Similarity	NPC129784
0.8321	Intermediate Similarity	NPC271945
0.8321	Intermediate Similarity	NPC476166
0.8321	Intermediate Similarity	NPC471517
0.8321	Intermediate Similarity	NPC17343
0.8321	Intermediate Similarity	NPC181497
0.8321	Intermediate Similarity	NPC206224
0.8321	Intermediate Similarity	NPC207892
0.8321	Intermediate Similarity	NPC284232
0.8321	Intermediate Similarity	NPC162801
0.8321	Intermediate Similarity	NPC150011
0.8321	Intermediate Similarity	NPC12875
0.8321	Intermediate Similarity	NPC236014
0.8321	Intermediate Similarity	NPC268917
0.8321	Intermediate Similarity	NPC129106
0.832	Intermediate Similarity	NPC212559
0.832	Intermediate Similarity	NPC473875
0.8308	Intermediate Similarity	NPC134360
0.8305	Intermediate Similarity	NPC75440
0.8305	Intermediate Similarity	NPC201959
0.8305	Intermediate Similarity	NPC169450
0.8305	Intermediate Similarity	NPC241549
0.8296	Intermediate Similarity	NPC471388
0.8295	Intermediate Similarity	NPC5428
0.8295	Intermediate Similarity	NPC469386
0.8295	Intermediate Similarity	NPC257947
0.8293	Intermediate Similarity	NPC50521
0.8293	Intermediate Similarity	NPC244816
0.8293	Intermediate Similarity	NPC221549
0.8286	Intermediate Similarity	NPC212142
0.8284	Intermediate Similarity	NPC477939
0.8284	Intermediate Similarity	NPC54743
0.8284	Intermediate Similarity	NPC173660
0.8284	Intermediate Similarity	NPC156502
0.8284	Intermediate Similarity	NPC265433
0.8284	Intermediate Similarity	NPC162659
0.8284	Intermediate Similarity	NPC29799
0.8284	Intermediate Similarity	NPC209985
0.8284	Intermediate Similarity	NPC263367
0.8284	Intermediate Similarity	NPC10737
0.8284	Intermediate Similarity	NPC270456
0.8284	Intermediate Similarity	NPC248727
0.8284	Intermediate Similarity	NPC177160
0.8281	Intermediate Similarity	NPC105031
0.8281	Intermediate Similarity	NPC170749
0.8279	Intermediate Similarity	NPC53906
0.8276	Intermediate Similarity	NPC323810
0.8276	Intermediate Similarity	NPC475225
0.8271	Intermediate Similarity	NPC115335
0.8271	Intermediate Similarity	NPC225696
0.8271	Intermediate Similarity	NPC198154
0.8271	Intermediate Similarity	NPC296915
0.8271	Intermediate Similarity	NPC473107
0.8271	Intermediate Similarity	NPC223008
0.8271	Intermediate Similarity	NPC97834
0.8268	Intermediate Similarity	NPC38761
0.8268	Intermediate Similarity	NPC76465
0.8264	Intermediate Similarity	NPC35344
0.8264	Intermediate Similarity	NPC141003
0.8264	Intermediate Similarity	NPC261343
0.8258	Intermediate Similarity	NPC230219
0.8254	Intermediate Similarity	NPC476633
0.8254	Intermediate Similarity	NPC475839
0.8254	Intermediate Similarity	NPC54972
0.8254	Intermediate Similarity	NPC193364
0.825	Intermediate Similarity	NPC275627
0.8244	Intermediate Similarity	NPC470727
0.8244	Intermediate Similarity	NPC27187
0.8244	Intermediate Similarity	NPC470225
0.8244	Intermediate Similarity	NPC196193
0.8235	Intermediate Similarity	NPC474272
0.8235	Intermediate Similarity	NPC472794
0.8235	Intermediate Similarity	NPC473049

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 NPC261992 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	918
0.2-0.3	1511
0.3-0.4	2583
0.4-0.5	1850
0.5-0.6	1118
0.6-0.7	711
0.7-0.8	170
0.8-0.85	8
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8739	High Similarity	NPD6671	Approved
0.8672	High Similarity	NPD6410	Clinical (unspecified phase)
0.856	High Similarity	NPD4749	Approved
0.845	Intermediate Similarity	NPD4625	Phase 3
0.8372	Intermediate Similarity	NPD4908	Phase 1
0.8295	Intermediate Similarity	NPD2861	Phase 2
0.8254	Intermediate Similarity	NPD1610	Phase 2
0.8244	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD7340	Approved
0.8136	Intermediate Similarity	NPD968	Approved
0.8125	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD4060	Phase 1
0.8062	Intermediate Similarity	NPD6696	Suspended
0.7985	Intermediate Similarity	NPD1613	Approved
0.7985	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD7157	Approved
0.7967	Intermediate Similarity	NPD1398	Phase 1
0.7956	Intermediate Similarity	NPD6099	Approved
0.7956	Intermediate Similarity	NPD6100	Approved
0.7937	Intermediate Similarity	NPD1548	Phase 1
0.7917	Intermediate Similarity	NPD290	Approved
0.7914	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD2232	Approved
0.7907	Intermediate Similarity	NPD2231	Phase 2
0.7907	Intermediate Similarity	NPD2230	Approved
0.7907	Intermediate Similarity	NPD2235	Phase 2
0.7907	Intermediate Similarity	NPD2233	Approved
0.7895	Intermediate Similarity	NPD3027	Phase 3
0.7891	Intermediate Similarity	NPD3496	Discontinued
0.7886	Intermediate Similarity	NPD7843	Approved
0.7886	Intermediate Similarity	NPD7635	Approved
0.7863	Intermediate Similarity	NPD2797	Approved
0.7851	Intermediate Similarity	NPD2684	Approved
0.7829	Intermediate Similarity	NPD1611	Approved
0.7823	Intermediate Similarity	NPD5283	Phase 1
0.782	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD6584	Phase 3
0.7787	Intermediate Similarity	NPD4750	Phase 3
0.777	Intermediate Similarity	NPD5763	Approved
0.777	Intermediate Similarity	NPD5762	Approved
0.7762	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD288	Approved
0.7744	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD5585	Approved
0.773	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD2238	Phase 2
0.771	Intermediate Similarity	NPD5327	Phase 3
0.7708	Intermediate Similarity	NPD6090	Discontinued
0.7704	Intermediate Similarity	NPD3268	Approved
0.7692	Intermediate Similarity	NPD1091	Approved
0.7674	Intermediate Similarity	NPD4626	Approved
0.7674	Intermediate Similarity	NPD1778	Approved
0.7672	Intermediate Similarity	NPD844	Approved
0.7664	Intermediate Similarity	NPD6355	Discontinued
0.7664	Intermediate Similarity	NPD5735	Approved
0.763	Intermediate Similarity	NPD7095	Approved
0.7627	Intermediate Similarity	NPD3020	Approved
0.7609	Intermediate Similarity	NPD4097	Suspended
0.7609	Intermediate Similarity	NPD6653	Approved
0.7609	Intermediate Similarity	NPD6353	Approved
0.7606	Intermediate Similarity	NPD3892	Phase 2
0.7597	Intermediate Similarity	NPD3444	Approved
0.7597	Intermediate Similarity	NPD5691	Approved
0.7597	Intermediate Similarity	NPD3443	Approved
0.7597	Intermediate Similarity	NPD3445	Approved
0.7591	Intermediate Similarity	NPD4140	Approved
0.7576	Intermediate Similarity	NPD6582	Phase 2
0.7576	Intermediate Similarity	NPD6583	Phase 3
0.7574	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD2557	Approved
0.7551	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD6674	Discontinued
0.7519	Intermediate Similarity	NPD8651	Approved
0.75	Intermediate Similarity	NPD4308	Phase 3
0.75	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD3022	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD1608	Approved
0.7481	Intermediate Similarity	NPD2237	Approved
0.7481	Intermediate Similarity	NPD1712	Approved
0.746	Intermediate Similarity	NPD5535	Approved
0.7448	Intermediate Similarity	NPD6087	Phase 1
0.7447	Intermediate Similarity	NPD6032	Approved
0.7447	Intermediate Similarity	NPD2935	Discontinued
0.7445	Intermediate Similarity	NPD7985	Registered
0.7444	Intermediate Similarity	NPD4359	Approved
0.7442	Intermediate Similarity	NPD7644	Approved
0.7422	Intermediate Similarity	NPD709	Approved
0.7422	Intermediate Similarity	NPD6387	Discontinued
0.7417	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD5177	Phase 3
0.7407	Intermediate Similarity	NPD4624	Approved
0.7407	Intermediate Similarity	NPD3690	Phase 2
0.7407	Intermediate Similarity	NPD3691	Phase 2
0.7405	Intermediate Similarity	NPD2667	Approved
0.7405	Intermediate Similarity	NPD5846	Approved
0.7405	Intermediate Similarity	NPD2668	Approved
0.7405	Intermediate Similarity	NPD6516	Phase 2
0.7391	Intermediate Similarity	NPD7265	Discontinued
0.7391	Intermediate Similarity	NPD7477	Discontinued
0.7388	Intermediate Similarity	NPD1283	Approved
0.7381	Intermediate Similarity	NPD228	Approved
0.7373	Intermediate Similarity	NPD2859	Approved
0.7373	Intermediate Similarity	NPD2860	Approved
0.7351	Intermediate Similarity	NPD5929	Approved
0.7343	Intermediate Similarity	NPD2424	Discontinued
0.7343	Intermediate Similarity	NPD7037	Approved
0.7339	Intermediate Similarity	NPD2342	Discontinued
0.7338	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3620	Phase 2
0.7338	Intermediate Similarity	NPD2979	Phase 3
0.7333	Intermediate Similarity	NPD3266	Approved
0.7333	Intermediate Similarity	NPD6362	Approved
0.7333	Intermediate Similarity	NPD3267	Approved
0.7329	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7041	Phase 2
0.7328	Intermediate Similarity	NPD3049	Approved
0.7328	Intermediate Similarity	NPD1651	Approved
0.7323	Intermediate Similarity	NPD821	Approved
0.7319	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD6798	Discontinued
0.7313	Intermediate Similarity	NPD3685	Discontinued
0.7305	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4538	Approved
0.7305	Intermediate Similarity	NPD4536	Approved
0.7305	Intermediate Similarity	NPD7097	Phase 1
0.7299	Intermediate Similarity	NPD596	Approved
0.7299	Intermediate Similarity	NPD6832	Phase 2
0.7299	Intermediate Similarity	NPD600	Approved
0.7293	Intermediate Similarity	NPD422	Phase 1
0.7288	Intermediate Similarity	NPD2934	Approved
0.7288	Intermediate Similarity	NPD2933	Approved
0.7286	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5124	Phase 1
0.7279	Intermediate Similarity	NPD558	Phase 2
0.7279	Intermediate Similarity	NPD7447	Phase 1
0.7279	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6002	Phase 3
0.7273	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD6005	Phase 3
0.7273	Intermediate Similarity	NPD6004	Phase 3
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD840	Approved
0.7266	Intermediate Similarity	NPD839	Approved
0.726	Intermediate Similarity	NPD6666	Approved
0.726	Intermediate Similarity	NPD6667	Approved
0.7259	Intermediate Similarity	NPD3225	Approved
0.7254	Intermediate Similarity	NPD2156	Approved
0.7254	Intermediate Similarity	NPD2154	Approved
0.7254	Intermediate Similarity	NPD2155	Approved
0.7252	Intermediate Similarity	NPD1182	Approved
0.7252	Intermediate Similarity	NPD3091	Approved
0.7241	Intermediate Similarity	NPD4628	Phase 3
0.7239	Intermediate Similarity	NPD1840	Phase 2
0.7234	Intermediate Similarity	NPD2157	Approved
0.7231	Intermediate Similarity	NPD3596	Phase 2
0.7222	Intermediate Similarity	NPD5451	Approved
0.7214	Intermediate Similarity	NPD4307	Phase 2
0.7214	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD1203	Approved
0.7206	Intermediate Similarity	NPD4098	Discontinued
0.7206	Intermediate Similarity	NPD3094	Phase 2
0.7203	Intermediate Similarity	NPD845	Approved
0.7203	Intermediate Similarity	NPD1551	Phase 2
0.7197	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2677	Approved
0.7188	Intermediate Similarity	NPD1138	Approved
0.7185	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD1535	Discovery
0.7164	Intermediate Similarity	NPD1281	Approved
0.7163	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7030	Discontinued
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD2554	Approved
0.7143	Intermediate Similarity	NPD4870	Approved
0.7143	Intermediate Similarity	NPD2556	Approved
0.7143	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6815	Approved
0.7133	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5960	Phase 3
0.7133	Intermediate Similarity	NPD4108	Discontinued
0.7133	Intermediate Similarity	NPD5588	Approved
0.7133	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2799	Discontinued
0.7124	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7466	Approved
0.7123	Intermediate Similarity	NPD4110	Phase 3
0.7123	Intermediate Similarity	NPD7976	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6580	Approved
0.7121	Intermediate Similarity	NPD1894	Discontinued
0.7121	Intermediate Similarity	NPD6581	Approved
0.7111	Intermediate Similarity	NPD1481	Phase 2

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