NPASS Compound

Structure

NPC470793 OpenBabel07101718242D 42 46 0 0 1 0 0 0 0 0999 V2000 0.9679 0.6549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5749 5.0591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2701 1.1443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4130 3.8383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5477 4.2956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0054 3.5903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1502 1.9361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3498 5.7166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0151 1.1934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1498 1.6507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9443 0.2414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9042 -0.4047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2149 4.2512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6150 1.7904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1203 1.1443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5749 4.0804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2701 2.1230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2169 0.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3023 0.4894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6063 3.3542 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9308 -0.3024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9122 1.5847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7961 5.0387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7919 0.7308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1203 2.1230 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7273 2.6123 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5749 2.1230 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5843 3.3176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9679 2.6123 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5749 1.1443 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7273 0.6549 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4225 3.5911 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1177 2.6123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6540 0.9463 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4047 5.9358 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6860 0.3327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7686 4.9291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5884 1.6881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7273 3.5911 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4225 2.6123 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 3.1655 2.5301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 8 37 1 0 0 0 0 9 10 2 0 0 0 0 9 22 1 0 0 0 0 10 29 1 0 0 0 0 11 18 2 0 0 0 0 11 24 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 0 0 0 0 13 20 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 38 1 0 0 0 0 16 32 2 0 0 0 0 16 39 1 0 0 0 0 17 33 2 0 0 0 0 17 40 1 0 0 0 0 18 19 1 0 0 0 0 19 30 1 1 0 0 0 20 28 1 0 0 0 0 20 29 1 1 0 0 0 21 31 1 1 0 0 0 21 41 1 0 0 0 0 22 34 2 0 0 0 0 22 42 1 0 0 0 0 23 35 2 0 0 0 0 23 37 1 0 0 0 0 24 36 2 0 0 0 0 24 38 1 0 0 0 0 25 15 1 6 0 0 0 25 26 1 0 0 0 0 25 29 1 0 0 0 0 26 27 1 0 0 0 0 26 39 1 6 0 0 0 27 30 1 1 0 0 0 27 40 1 0 0 0 0 28 42 1 0 0 0 0 29 6 1 1 0 0 0 30 31 1 1 0 0 0 31 15 1 1 0 0 0 31 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.24
Volume:	577.551
LogP:	3.152
LogD:	1.465
LogS:	-4.211
# Rotatable Bonds:	9
TPSA:	151.1
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.225
Synthetic Accessibility Score:	6.037
Fsp3:	0.613
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:	-5.392
MDCK Permeability:	7.695902604609728e-05
Pgp-inhibitor:	0.887
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.756
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.802

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	66.90299224853516%
Volume Distribution (VD):	0.862
Pgp-substrate:	27.000707626342773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.057
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.09
CYP2C9-inhibitor:	0.673
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.087
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.689
CYP3A4-substrate:	0.479

ADMET: Excretion

Clearance (CL):	5.307
Half-life (T1/2):	0.884

ADMET: Toxicity

hERG Blockers:	0.367
Human Hepatotoxicity (H-HT):	0.95
Drug-inuced Liver Injury (DILI):	0.741
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.818
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.106
Carcinogencity:	0.03
Eye Corrosion:	0.004
Eye Irritation:	0.03
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC470793

Natural Product ID:	NPC470793
*Common Name:**	Munronoid O
IUPAC Name:	methyl 2-[(3R,4R)-4-[(1aR,3S,3aR,4R,5R,6R,7aS)-4,5-diacetyloxy-3a-methyl-7-methylidene-3-(5-oxo-2H-furan-3-yl)-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-6-yl]-2,2,4-trimethyl-7-oxo-3H-oxepin-3-yl]acetate
Synonyms:
Standard InCHIKey:	CIAQJXVCRASXDX-JZGLTLKLSA-N
Standard InCHI:	InChI=1S/C31H38O11/c1-15-25(29(6)10-9-22(34)42-28(4,5)20(29)13-23(35)37-8)26(39-16(2)32)27(40-17(3)33)30(7)19(12-21-31(15,30)41-21)18-11-24(36)38-14-18/h9-11,19-21,25-27H,1,12-14H2,2-8H3/t19-,20-,21+,25+,26+,27-,29-,30+,31+/m0/s1
SMILES:	CC(=O)OC1C(C(=C)C23C(O2)CC(C3(C1OC(=O)C)C)C4=CC(=O)OC4)C5(C=CC(=O)OC(C5CC(=O)OC)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229169
PubChem CID:	76311479
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic 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
NPO33254	munronia unifoliolata oliv	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22500574]

☑ 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
Others	8

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	IC50	=	22.2	ug.mL-1	PMID[569116]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	11.2	%	PMID[569116]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	24.6	%	PMID[569116]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	33.4	%	PMID[569116]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	42.8	%	PMID[569116]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	51.4	%	PMID[569116]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	64.2	%	PMID[569116]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	50.2	%	PMID[569116]

☑ 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 NPC470793 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	275
0.1-0.2	1582
0.2-0.3	4909
0.3-0.4	8963
0.4-0.5	13118
0.5-0.6	7469
0.6-0.7	5027
0.7-0.8	1267
0.8-0.85	74
0.85-0.9	8
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9636	High Similarity	NPC4548
0.9369	High Similarity	NPC472667
0.9286	High Similarity	NPC143755
0.9279	High Similarity	NPC159928
0.906	High Similarity	NPC470850
0.8983	High Similarity	NPC470851
0.8707	High Similarity	NPC310511
0.8609	High Similarity	NPC470420
0.8512	High Similarity	NPC104382
0.8512	High Similarity	NPC175186
0.848	Intermediate Similarity	NPC246209
0.8443	Intermediate Similarity	NPC471170
0.8413	Intermediate Similarity	NPC476558
0.8393	Intermediate Similarity	NPC471934
0.8376	Intermediate Similarity	NPC312536
0.8361	Intermediate Similarity	NPC475371
0.8361	Intermediate Similarity	NPC231529
0.8348	Intermediate Similarity	NPC90472
0.8319	Intermediate Similarity	NPC257017
0.8319	Intermediate Similarity	NPC162009
0.8305	Intermediate Similarity	NPC157252
0.8305	Intermediate Similarity	NPC471128
0.8305	Intermediate Similarity	NPC471126
0.8305	Intermediate Similarity	NPC145182
0.8291	Intermediate Similarity	NPC124676
0.8291	Intermediate Similarity	NPC475372
0.8291	Intermediate Similarity	NPC146280
0.8288	Intermediate Similarity	NPC470975
0.8288	Intermediate Similarity	NPC103088
0.8288	Intermediate Similarity	NPC470979
0.8276	Intermediate Similarity	NPC154363
0.8276	Intermediate Similarity	NPC234858
0.8276	Intermediate Similarity	NPC471127
0.825	Intermediate Similarity	NPC473979
0.825	Intermediate Similarity	NPC129992
0.8235	Intermediate Similarity	NPC52839
0.823	Intermediate Similarity	NPC469370
0.822	Intermediate Similarity	NPC475520
0.822	Intermediate Similarity	NPC236918
0.822	Intermediate Similarity	NPC156745
0.8205	Intermediate Similarity	NPC10721
0.8197	Intermediate Similarity	NPC287423
0.819	Intermediate Similarity	NPC43213
0.819	Intermediate Similarity	NPC216665
0.8182	Intermediate Similarity	NPC145238
0.8174	Intermediate Similarity	NPC471933
0.8158	Intermediate Similarity	NPC253906
0.8151	Intermediate Similarity	NPC475885
0.8151	Intermediate Similarity	NPC329080
0.8151	Intermediate Similarity	NPC472759
0.8151	Intermediate Similarity	NPC472004
0.8136	Intermediate Similarity	NPC473720
0.8136	Intermediate Similarity	NPC472397
0.8136	Intermediate Similarity	NPC171905
0.8136	Intermediate Similarity	NPC471125
0.8136	Intermediate Similarity	NPC472758
0.8125	Intermediate Similarity	NPC470980
0.8115	Intermediate Similarity	NPC473635
0.8103	Intermediate Similarity	NPC472757
0.8099	Intermediate Similarity	NPC469352
0.8099	Intermediate Similarity	NPC472399
0.8099	Intermediate Similarity	NPC473802
0.8073	Intermediate Similarity	NPC107806
0.8073	Intermediate Similarity	NPC72647
0.8067	Intermediate Similarity	NPC5991
0.8067	Intermediate Similarity	NPC22628
0.8067	Intermediate Similarity	NPC5989
0.8067	Intermediate Similarity	NPC469380
0.8067	Intermediate Similarity	NPC275696
0.8067	Intermediate Similarity	NPC471108
0.8067	Intermediate Similarity	NPC255081
0.8056	Intermediate Similarity	NPC209297
0.8056	Intermediate Similarity	NPC475380
0.8053	Intermediate Similarity	NPC180744
0.8051	Intermediate Similarity	NPC473656
0.8036	Intermediate Similarity	NPC477127
0.8034	Intermediate Similarity	NPC472400
0.8034	Intermediate Similarity	NPC178289
0.8033	Intermediate Similarity	NPC473709
0.8033	Intermediate Similarity	NPC473919
0.8018	Intermediate Similarity	NPC470972
0.8017	Intermediate Similarity	NPC475391
0.8017	Intermediate Similarity	NPC470265
0.8017	Intermediate Similarity	NPC170538
0.8017	Intermediate Similarity	NPC23786
0.8	Intermediate Similarity	NPC472214
0.8	Intermediate Similarity	NPC472215
0.8	Intermediate Similarity	NPC151616
0.7982	Intermediate Similarity	NPC475446
0.7982	Intermediate Similarity	NPC311241
0.7982	Intermediate Similarity	NPC100912
0.7967	Intermediate Similarity	NPC471939
0.7967	Intermediate Similarity	NPC293112
0.7966	Intermediate Similarity	NPC477509
0.7951	Intermediate Similarity	NPC6193
0.7951	Intermediate Similarity	NPC11895
0.7949	Intermediate Similarity	NPC477126
0.7949	Intermediate Similarity	NPC473535
0.7949	Intermediate Similarity	NPC470120
0.7949	Intermediate Similarity	NPC474937
0.7937	Intermediate Similarity	NPC472769
0.7934	Intermediate Similarity	NPC472401
0.7934	Intermediate Similarity	NPC67569
0.7934	Intermediate Similarity	NPC204731
0.7931	Intermediate Similarity	NPC174471
0.7931	Intermediate Similarity	NPC474871
0.7931	Intermediate Similarity	NPC194619
0.7931	Intermediate Similarity	NPC470076
0.7931	Intermediate Similarity	NPC260786
0.7931	Intermediate Similarity	NPC96739
0.792	Intermediate Similarity	NPC472770
0.7917	Intermediate Similarity	NPC5292
0.7903	Intermediate Similarity	NPC471940
0.7899	Intermediate Similarity	NPC156252
0.7899	Intermediate Similarity	NPC475323
0.7895	Intermediate Similarity	NPC67321
0.7895	Intermediate Similarity	NPC475510
0.7895	Intermediate Similarity	NPC187435
0.7895	Intermediate Similarity	NPC471601
0.7895	Intermediate Similarity	NPC475587
0.7895	Intermediate Similarity	NPC474716
0.7886	Intermediate Similarity	NPC172154
0.7886	Intermediate Similarity	NPC8374
0.7886	Intermediate Similarity	NPC81736
0.7881	Intermediate Similarity	NPC73314
0.7881	Intermediate Similarity	NPC474872
0.7876	Intermediate Similarity	NPC474550
0.7876	Intermediate Similarity	NPC475585
0.7876	Intermediate Similarity	NPC473577
0.787	Intermediate Similarity	NPC161998
0.787	Intermediate Similarity	NPC140277
0.7869	Intermediate Similarity	NPC19464
0.7869	Intermediate Similarity	NPC222688
0.7863	Intermediate Similarity	NPC170212
0.7863	Intermediate Similarity	NPC89227
0.7863	Intermediate Similarity	NPC221511
0.7863	Intermediate Similarity	NPC17138
0.7863	Intermediate Similarity	NPC101825
0.7863	Intermediate Similarity	NPC151216
0.7863	Intermediate Similarity	NPC215643
0.7863	Intermediate Similarity	NPC470063
0.7863	Intermediate Similarity	NPC265499
0.7857	Intermediate Similarity	NPC475389
0.7857	Intermediate Similarity	NPC476081
0.7857	Intermediate Similarity	NPC472552
0.7857	Intermediate Similarity	NPC473838
0.7851	Intermediate Similarity	NPC145074
0.7851	Intermediate Similarity	NPC474585
0.7851	Intermediate Similarity	NPC41123
0.7851	Intermediate Similarity	NPC185876
0.7851	Intermediate Similarity	NPC114939
0.7851	Intermediate Similarity	NPC474370
0.7851	Intermediate Similarity	NPC19336
0.7845	Intermediate Similarity	NPC473975
0.7845	Intermediate Similarity	NPC473594
0.7845	Intermediate Similarity	NPC474586
0.7845	Intermediate Similarity	NPC281624
0.7845	Intermediate Similarity	NPC473843
0.784	Intermediate Similarity	NPC270109
0.784	Intermediate Similarity	NPC236999
0.7833	Intermediate Similarity	NPC153440
0.7826	Intermediate Similarity	NPC473939
0.7826	Intermediate Similarity	NPC181994
0.7826	Intermediate Similarity	NPC473595
0.7826	Intermediate Similarity	NPC94377
0.7823	Intermediate Similarity	NPC15095
0.7823	Intermediate Similarity	NPC470973
0.7815	Intermediate Similarity	NPC196931
0.7815	Intermediate Similarity	NPC470075
0.7815	Intermediate Similarity	NPC138372
0.7815	Intermediate Similarity	NPC190286
0.7815	Intermediate Similarity	NPC106228
0.7812	Intermediate Similarity	NPC476823
0.7807	Intermediate Similarity	NPC469874
0.7807	Intermediate Similarity	NPC475290
0.7805	Intermediate Similarity	NPC469789
0.7805	Intermediate Similarity	NPC469382
0.7797	Intermediate Similarity	NPC71889
0.7795	Intermediate Similarity	NPC475139
0.7795	Intermediate Similarity	NPC180902
0.7795	Intermediate Similarity	NPC34963
0.7787	Intermediate Similarity	NPC312481
0.7778	Intermediate Similarity	NPC469655
0.7778	Intermediate Similarity	NPC469656
0.7778	Intermediate Similarity	NPC471407
0.7778	Intermediate Similarity	NPC35109
0.7778	Intermediate Similarity	NPC474846
0.7769	Intermediate Similarity	NPC264954
0.7769	Intermediate Similarity	NPC470186
0.7769	Intermediate Similarity	NPC19028
0.7769	Intermediate Similarity	NPC9674
0.7769	Intermediate Similarity	NPC180640
0.7769	Intermediate Similarity	NPC475041
0.7768	Intermediate Similarity	NPC472554
0.7759	Intermediate Similarity	NPC273433
0.7759	Intermediate Similarity	NPC284828
0.7759	Intermediate Similarity	NPC173905
0.7759	Intermediate Similarity	NPC472216
0.7759	Intermediate Similarity	NPC5475
0.775	Intermediate Similarity	NPC469684

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 NPC470793 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	1932
0.2-0.3	3878
0.3-0.4	2081
0.4-0.5	616
0.5-0.6	235
0.6-0.7	155
0.7-0.8	17
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8053	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD6008	Approved
0.7623	Intermediate Similarity	NPD7516	Approved
0.7607	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD7115	Discovery
0.7541	Intermediate Similarity	NPD7327	Approved
0.7541	Intermediate Similarity	NPD7328	Approved
0.754	Intermediate Similarity	NPD7507	Approved
0.7522	Intermediate Similarity	NPD6648	Approved
0.75	Intermediate Similarity	NPD7319	Approved
0.7456	Intermediate Similarity	NPD5344	Discontinued
0.7339	Intermediate Similarity	NPD1695	Approved
0.7288	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD7638	Approved
0.7273	Intermediate Similarity	NPD8297	Approved
0.725	Intermediate Similarity	NPD6371	Approved
0.7222	Intermediate Similarity	NPD8296	Approved
0.7222	Intermediate Similarity	NPD8378	Approved
0.7222	Intermediate Similarity	NPD8379	Approved
0.7222	Intermediate Similarity	NPD8335	Approved
0.7222	Intermediate Similarity	NPD8033	Approved
0.7222	Intermediate Similarity	NPD8380	Approved
0.7217	Intermediate Similarity	NPD7639	Approved
0.7217	Intermediate Similarity	NPD7640	Approved
0.719	Intermediate Similarity	NPD6649	Approved
0.719	Intermediate Similarity	NPD6650	Approved
0.7168	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8294	Approved
0.7143	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD8377	Approved
0.7131	Intermediate Similarity	NPD6053	Discontinued
0.7083	Intermediate Similarity	NPD6686	Approved
0.7083	Intermediate Similarity	NPD6899	Approved
0.7083	Intermediate Similarity	NPD6881	Approved
0.7073	Intermediate Similarity	NPD4632	Approved
0.7054	Intermediate Similarity	NPD7492	Approved
0.7025	Intermediate Similarity	NPD6372	Approved
0.7025	Intermediate Similarity	NPD6373	Approved
0.7008	Intermediate Similarity	NPD6054	Approved
0.7	Intermediate Similarity	NPD5697	Approved
0.7	Intermediate Similarity	NPD6616	Approved
0.6992	Remote Similarity	NPD6882	Approved
0.6977	Remote Similarity	NPD7604	Phase 2
0.6967	Remote Similarity	NPD6883	Approved
0.6967	Remote Similarity	NPD7290	Approved
0.6967	Remote Similarity	NPD7102	Approved
0.6964	Remote Similarity	NPD46	Approved
0.6964	Remote Similarity	NPD6698	Approved
0.6953	Remote Similarity	NPD7503	Approved
0.6947	Remote Similarity	NPD7078	Approved
0.6942	Remote Similarity	NPD7320	Approved
0.6917	Remote Similarity	NPD6675	Approved
0.6917	Remote Similarity	NPD7128	Approved
0.6917	Remote Similarity	NPD5739	Approved
0.6917	Remote Similarity	NPD6402	Approved
0.6911	Remote Similarity	NPD6847	Approved
0.6911	Remote Similarity	NPD6869	Approved
0.6911	Remote Similarity	NPD8130	Phase 1
0.6911	Remote Similarity	NPD6617	Approved
0.6905	Remote Similarity	NPD6009	Approved
0.6899	Remote Similarity	NPD6370	Approved
0.6894	Remote Similarity	NPD7736	Approved
0.6885	Remote Similarity	NPD6012	Approved
0.6885	Remote Similarity	NPD6014	Approved
0.6885	Remote Similarity	NPD6013	Approved
0.6852	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4225	Approved
0.6822	Remote Similarity	NPD6015	Approved
0.6822	Remote Similarity	NPD5983	Phase 2
0.6822	Remote Similarity	NPD6016	Approved
0.6818	Remote Similarity	NPD1694	Approved
0.6803	Remote Similarity	NPD6011	Approved
0.6803	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6903	Approved
0.6783	Remote Similarity	NPD6001	Approved
0.6769	Remote Similarity	NPD5988	Approved
0.6757	Remote Similarity	NPD7521	Approved
0.6757	Remote Similarity	NPD7334	Approved
0.6757	Remote Similarity	NPD5330	Approved
0.6757	Remote Similarity	NPD6684	Approved
0.6757	Remote Similarity	NPD7146	Approved
0.6757	Remote Similarity	NPD6409	Approved
0.6754	Remote Similarity	NPD5693	Phase 1
0.6744	Remote Similarity	NPD6059	Approved
0.6742	Remote Similarity	NPD6336	Discontinued
0.6721	Remote Similarity	NPD5701	Approved
0.6696	Remote Similarity	NPD6399	Phase 3
0.6692	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6639	Remote Similarity	NPD4696	Approved
0.6639	Remote Similarity	NPD5286	Approved
0.6639	Remote Similarity	NPD5285	Approved
0.6637	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6083	Phase 2
0.661	Remote Similarity	NPD6084	Phase 2
0.6585	Remote Similarity	NPD6412	Phase 2
0.6583	Remote Similarity	NPD1700	Approved
0.6581	Remote Similarity	NPD5695	Phase 3
0.6579	Remote Similarity	NPD6080	Approved
0.6579	Remote Similarity	NPD6051	Approved
0.6579	Remote Similarity	NPD6904	Approved
0.6579	Remote Similarity	NPD6673	Approved
0.656	Remote Similarity	NPD4634	Approved
0.6557	Remote Similarity	NPD5141	Approved
0.6555	Remote Similarity	NPD5696	Approved
0.6538	Remote Similarity	NPD7101	Approved
0.6538	Remote Similarity	NPD7100	Approved
0.6535	Remote Similarity	NPD8133	Approved
0.6529	Remote Similarity	NPD5225	Approved
0.6529	Remote Similarity	NPD4633	Approved
0.6529	Remote Similarity	NPD5226	Approved
0.6529	Remote Similarity	NPD5224	Approved
0.6508	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD7900	Approved
0.6496	Remote Similarity	NPD7260	Phase 2
0.6496	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5737	Approved
0.6491	Remote Similarity	NPD6672	Approved
0.6475	Remote Similarity	NPD5174	Approved
0.6475	Remote Similarity	NPD5175	Approved
0.6471	Remote Similarity	NPD4755	Approved
0.6466	Remote Similarity	NPD5694	Approved
0.6466	Remote Similarity	NPD5281	Approved
0.6466	Remote Similarity	NPD5284	Approved
0.6466	Remote Similarity	NPD6050	Approved
0.6462	Remote Similarity	NPD6335	Approved
0.6446	Remote Similarity	NPD5223	Approved
0.6441	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6274	Approved
0.641	Remote Similarity	NPD4202	Approved
0.64	Remote Similarity	NPD4729	Approved
0.64	Remote Similarity	NPD4730	Approved
0.6385	Remote Similarity	NPD6317	Approved
0.6379	Remote Similarity	NPD5692	Phase 3
0.6364	Remote Similarity	NPD4700	Approved
0.6348	Remote Similarity	NPD5208	Approved
0.6339	Remote Similarity	NPD5362	Discontinued
0.6336	Remote Similarity	NPD6313	Approved
0.6336	Remote Similarity	NPD6314	Approved
0.6333	Remote Similarity	NPD7902	Approved
0.6331	Remote Similarity	NPD8338	Approved
0.6325	Remote Similarity	NPD6079	Approved
0.6325	Remote Similarity	NPD7637	Suspended
0.6325	Remote Similarity	NPD8034	Phase 2
0.6325	Remote Similarity	NPD8035	Phase 2
0.6316	Remote Similarity	NPD6098	Approved
0.6316	Remote Similarity	NPD6921	Approved
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	NPD5250	Approved
0.6299	Remote Similarity	NPD5251	Approved
0.6299	Remote Similarity	NPD5247	Approved
0.6281	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6033	Approved
0.6261	Remote Similarity	NPD4251	Approved
0.6261	Remote Similarity	NPD3573	Approved
0.6261	Remote Similarity	NPD4250	Approved
0.624	Remote Similarity	NPD4768	Approved
0.624	Remote Similarity	NPD4767	Approved
0.6228	Remote Similarity	NPD5363	Approved
0.6228	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6067	Discontinued
0.622	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5282	Discontinued
0.6218	Remote Similarity	NPD7748	Approved
0.6214	Remote Similarity	NPD6845	Suspended
0.621	Remote Similarity	NPD6052	Approved
0.6194	Remote Similarity	NPD6909	Approved
0.6194	Remote Similarity	NPD8513	Phase 3
0.6194	Remote Similarity	NPD6908	Approved
0.6194	Remote Similarity	NPD8517	Approved
0.6194	Remote Similarity	NPD8516	Approved
0.6194	Remote Similarity	NPD8515	Approved
0.619	Remote Similarity	NPD6614	Approved
0.6174	Remote Similarity	NPD4249	Approved
0.6174	Remote Similarity	NPD3618	Phase 1
0.6154	Remote Similarity	NPD5328	Approved
0.6154	Remote Similarity	NPD4753	Phase 2
0.6142	Remote Similarity	NPD5128	Approved
0.6124	Remote Similarity	NPD5216	Approved
0.6124	Remote Similarity	NPD5217	Approved
0.6124	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD5215	Approved
0.6121	Remote Similarity	NPD7524	Approved
0.6116	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD5222	Approved
0.6116	Remote Similarity	NPD5221	Approved
0.6106	Remote Similarity	NPD5209	Approved
0.6103	Remote Similarity	NPD8328	Phase 3
0.6102	Remote Similarity	NPD3168	Discontinued
0.608	Remote Similarity	NPD4754	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