NPASS Compound

Structure

NPC101400 OpenBabel07101719152D 38 42 0 0 1 0 0 0 0 0999 V2000 -0.0922 1.6794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3257 0.1894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7345 -2.6103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1443 -1.8005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1707 -3.4269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6144 -3.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6510 -3.1126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0423 -3.5213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7158 0.3194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0019 -0.9996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7158 -0.4007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1887 -1.5423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5314 0.3194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1769 -2.3234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5142 -0.3717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9972 0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0922 0.6794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6490 -0.5469 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8830 -3.1346 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0032 -2.6594 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1797 -2.3981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5314 -0.4007 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4140 -1.3519 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5165 -3.2912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1682 -0.2333 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6116 -0.0929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1995 -1.4728 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0922 -0.7608 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5633 -0.8262 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9114 -4.1342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0298 -4.1288 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5692 0.6828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6934 0.9038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1891 -2.1163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0396 -0.1407 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 1.2017 -0.6638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0939 -2.9027 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 5 7 2 0 0 0 0 6 8 2 0 0 0 0 7 20 1 0 0 0 0 8 24 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 12 34 1 0 0 0 0 13 17 2 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 14 23 1 0 0 0 0 15 28 1 0 0 0 0 15 35 1 0 0 0 0 16 29 1 0 0 0 0 16 36 1 0 0 0 0 18 2 1 1 0 0 0 18 25 1 0 0 0 0 19 3 1 1 0 0 0 19 30 1 0 0 0 0 20 19 1 6 0 0 0 20 34 1 0 0 0 0 21 27 1 1 0 0 0 21 38 1 0 0 0 0 22 28 1 1 0 0 0 22 37 1 0 0 0 0 23 29 1 1 0 0 0 23 37 1 0 0 0 0 24 31 2 0 0 0 0 24 38 1 0 0 0 0 25 26 1 0 0 0 0 25 32 1 6 0 0 0 26 33 2 0 0 0 0 26 35 1 0 0 0 0 27 28 1 6 0 0 0 28 11 1 1 0 0 0 29 27 1 6 0 0 0 29 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.27
Volume:	533.287
LogP:	2.06
LogD:	0.91
LogS:	-3.4
# Rotatable Bonds:	1
TPSA:	124.05
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.298
Synthetic Accessibility Score:	7.403
Fsp3:	0.724
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.214
MDCK Permeability:	1.4204026228981093e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.3

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.126
Plasma Protein Binding (PPB):	84.6998062133789%
Volume Distribution (VD):	1.48
Pgp-substrate:	8.612829208374023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.668
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.573
CYP3A4-substrate:	0.477

ADMET: Excretion

Clearance (CL):	2.343
Half-life (T1/2):	0.846

ADMET: Toxicity

hERG Blockers:	0.688
Human Hepatotoxicity (H-HT):	0.87
Drug-inuced Liver Injury (DILI):	0.693
AMES Toxicity:	0.667
Rat Oral Acute Toxicity:	0.794
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.55
Carcinogencity:	0.13
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC101400

Natural Product ID:	NPC101400
*Common Name:**	(6'r,13's) Isororidin A
IUPAC Name:	n.a.
Synonyms:	(6'R,13'S) Isororidin A
Standard InCHIKey:	NSFWWJIQIKBZMJ-NYUDFZJYSA-N
Standard InCHI:	InChI=1S/C29H40O9/c1-17-9-11-28-15-35-26(33)25(32)18(2)10-12-34-20(19(3)30)7-5-6-8-24(31)38-21-14-23(37-22(28)13-17)29(16-36-29)27(21,28)4/h5-8,13,18-23,25,30,32H,9-12,14-16H2,1-4H3/b7-5+,8-6-/t18-,19+,20-,21-,22-,23-,25+,27-,28-,29+/m1/s1
SMILES:	CC1=C[C@@H]2[C@@]3(CC1)COC(=O)[C@H]([C@H](C)CCO[C@H](/C=C/C=CC(=O)O[C@@H]1C[C@H]([C@@]4(CO4)[C@@]31C)O2)[C@H](C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL341800
PubChem CID:	73352797
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001789] Trichothecenes

*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
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075777]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[13678412]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21539317]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	17
Others	7

Activity Type	# Activity
Cell Line	20
CELL-LINE	1
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT730	Cell Line	MC-38	Mus musculus	Selectivity	=	-500.0	zone unit	PMID[476075]
NPT730	Cell Line	MC-38	Mus musculus	Selectivity	=	-50.0	zone unit	PMID[476075]
NPT137	Cell Line	L1210	Mus musculus	Selectivity	=	450.0	zone unit	PMID[476075]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	>	10000.0	nM	PMID[476075]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[476075]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	>	10000.0	nM	PMID[476075]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[476075]
NPT455	Cell Line	NCI-H522	Homo sapiens	IC50	=	95.0	nM	PMID[476075]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	8.0	nM	PMID[476075]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000.0	nM	PMID[476075]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	>	10000.0	nM	PMID[476075]
NPT387	Cell Line	M14	Homo sapiens	IC50	=	10.0	nM	PMID[476075]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	10000.0	nM	PMID[476075]
NPT398	Cell Line	UACC-62	Homo sapiens	IC50	=	2.0	nM	PMID[476075]
NPT401	Cell Line	786-0	Homo sapiens	IC50	>	10000.0	nM	PMID[476075]
NPT376	Cell Line	A498	Homo sapiens	IC50	=	6.0	nM	PMID[476075]
NPT406	Cell Line	RXF 393	Homo sapiens	IC50	=	10.0	nM	PMID[476075]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[476075]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	31.0	nM	PMID[476075]
NPT367	Cell Line	MDA-N	Homo sapiens	IC50	=	8.0	nM	PMID[476075]
NPT2	Others	Unspecified		Relative activity	=	1066.0	n.a.	PMID[476075]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Concentration	=	0.9	ug ml-1	PMID[476075]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Selectivity	=	-150.0	zone unit	PMID[476075]
NPT22117	CELL-LINE	NCI-H125	Homo sapiens	Selectivity	=	-150.0	zone unit	PMID[476075]

☑ 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 NPC101400 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	208
0.1-0.2	1103
0.2-0.3	4090
0.3-0.4	7911
0.4-0.5	14186
0.5-0.6	7964
0.6-0.7	5777
0.7-0.8	1362
0.8-0.85	41
0.85-0.9	33
0.9-0.95	15
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC101965
0.9904	High Similarity	NPC98038
0.9904	High Similarity	NPC313921
0.9533	High Similarity	NPC265290
0.9533	High Similarity	NPC305044
0.9327	High Similarity	NPC93026
0.9327	High Similarity	NPC29389
0.9327	High Similarity	NPC265502
0.9327	High Similarity	NPC469960
0.9238	High Similarity	NPC469957
0.9238	High Similarity	NPC472263
0.9238	High Similarity	NPC469959
0.9238	High Similarity	NPC108682
0.8929	High Similarity	NPC474286
0.8929	High Similarity	NPC475130
0.8857	High Similarity	NPC475956
0.8857	High Similarity	NPC214714
0.8857	High Similarity	NPC200672
0.8857	High Similarity	NPC252242
0.8846	High Similarity	NPC79631
0.8846	High Similarity	NPC13743
0.8846	High Similarity	NPC98813
0.8807	High Similarity	NPC41551
0.8807	High Similarity	NPC50223
0.8774	High Similarity	NPC474783
0.8774	High Similarity	NPC260809
0.8762	High Similarity	NPC26557
0.875	High Similarity	NPC65700
0.8739	High Similarity	NPC287075
0.8598	High Similarity	NPC232515
0.8571	High Similarity	NPC474957
0.8571	High Similarity	NPC79449
0.8559	High Similarity	NPC71680
0.8545	High Similarity	NPC77089
0.8505	High Similarity	NPC475986
0.8482	Intermediate Similarity	NPC241477
0.8476	Intermediate Similarity	NPC476057
0.8476	Intermediate Similarity	NPC347923
0.8468	Intermediate Similarity	NPC15551
0.8462	Intermediate Similarity	NPC240838
0.8396	Intermediate Similarity	NPC274458
0.8349	Intermediate Similarity	NPC169843
0.8302	Intermediate Similarity	NPC120299
0.8302	Intermediate Similarity	NPC182811
0.8276	Intermediate Similarity	NPC475401
0.8257	Intermediate Similarity	NPC123505
0.8246	Intermediate Similarity	NPC469496
0.8246	Intermediate Similarity	NPC469463
0.8246	Intermediate Similarity	NPC469454
0.8224	Intermediate Similarity	NPC475653
0.8208	Intermediate Similarity	NPC255410
0.8205	Intermediate Similarity	NPC477092
0.8198	Intermediate Similarity	NPC470192
0.819	Intermediate Similarity	NPC475305
0.8165	Intermediate Similarity	NPC473596
0.8136	Intermediate Similarity	NPC79579
0.8113	Intermediate Similarity	NPC300710
0.807	Intermediate Similarity	NPC179798
0.807	Intermediate Similarity	NPC304180
0.8051	Intermediate Similarity	NPC305260
0.8051	Intermediate Similarity	NPC5292
0.8051	Intermediate Similarity	NPC270850
0.8051	Intermediate Similarity	NPC278681
0.8017	Intermediate Similarity	NPC216665
0.7983	Intermediate Similarity	NPC112936
0.7982	Intermediate Similarity	NPC5103
0.7982	Intermediate Similarity	NPC475053
0.7982	Intermediate Similarity	NPC181298
0.7966	Intermediate Similarity	NPC153440
0.7966	Intermediate Similarity	NPC13710
0.7966	Intermediate Similarity	NPC16701
0.7946	Intermediate Similarity	NPC470980
0.7937	Intermediate Similarity	NPC471234
0.7934	Intermediate Similarity	NPC6193
0.7931	Intermediate Similarity	NPC56448
0.7917	Intermediate Similarity	NPC473228
0.7917	Intermediate Similarity	NPC312481
0.7917	Intermediate Similarity	NPC470829
0.7913	Intermediate Similarity	NPC475495
0.7903	Intermediate Similarity	NPC470880
0.7899	Intermediate Similarity	NPC35171
0.7899	Intermediate Similarity	NPC213761
0.7895	Intermediate Similarity	NPC475274
0.789	Intermediate Similarity	NPC222303
0.7881	Intermediate Similarity	NPC157380
0.7881	Intermediate Similarity	NPC23046
0.7881	Intermediate Similarity	NPC185287
0.7876	Intermediate Similarity	NPC324327
0.7876	Intermediate Similarity	NPC194620
0.7876	Intermediate Similarity	NPC326994
0.7876	Intermediate Similarity	NPC72813
0.7876	Intermediate Similarity	NPC474421
0.7863	Intermediate Similarity	NPC43213
0.7863	Intermediate Similarity	NPC178289
0.7857	Intermediate Similarity	NPC472748
0.7851	Intermediate Similarity	NPC107493
0.7851	Intermediate Similarity	NPC471082
0.7845	Intermediate Similarity	NPC317687
0.7845	Intermediate Similarity	NPC475277
0.7845	Intermediate Similarity	NPC473522
0.7845	Intermediate Similarity	NPC477093
0.784	Intermediate Similarity	NPC213634
0.7833	Intermediate Similarity	NPC474585
0.7807	Intermediate Similarity	NPC169888
0.7807	Intermediate Similarity	NPC474664
0.7807	Intermediate Similarity	NPC327286
0.7807	Intermediate Similarity	NPC55972
0.7807	Intermediate Similarity	NPC233379
0.7807	Intermediate Similarity	NPC14862
0.7805	Intermediate Similarity	NPC159499
0.7797	Intermediate Similarity	NPC148458
0.7797	Intermediate Similarity	NPC190286
0.7788	Intermediate Similarity	NPC54737
0.7788	Intermediate Similarity	NPC9303
0.7788	Intermediate Similarity	NPC472749
0.7788	Intermediate Similarity	NPC477125
0.7788	Intermediate Similarity	NPC472751
0.7788	Intermediate Similarity	NPC16313
0.7778	Intermediate Similarity	NPC471855
0.7769	Intermediate Similarity	NPC472000
0.7769	Intermediate Similarity	NPC46570
0.7769	Intermediate Similarity	NPC471999
0.7769	Intermediate Similarity	NPC310511
0.7768	Intermediate Similarity	NPC4620
0.7768	Intermediate Similarity	NPC472750
0.7768	Intermediate Similarity	NPC183570
0.7768	Intermediate Similarity	NPC472747
0.776	Intermediate Similarity	NPC471407
0.7759	Intermediate Similarity	NPC474750
0.7759	Intermediate Similarity	NPC317107
0.775	Intermediate Similarity	NPC472667
0.7748	Intermediate Similarity	NPC146822
0.7742	Intermediate Similarity	NPC473253
0.7742	Intermediate Similarity	NPC473265
0.7739	Intermediate Similarity	NPC139838
0.7739	Intermediate Similarity	NPC15218
0.7739	Intermediate Similarity	NPC59489
0.7736	Intermediate Similarity	NPC197107
0.7734	Intermediate Similarity	NPC158350
0.7731	Intermediate Similarity	NPC239273
0.7727	Intermediate Similarity	NPC161855
0.7706	Intermediate Similarity	NPC57664
0.7705	Intermediate Similarity	NPC23786
0.7705	Intermediate Similarity	NPC470265
0.7699	Intermediate Similarity	NPC475676
0.7699	Intermediate Similarity	NPC220964
0.7692	Intermediate Similarity	NPC126691
0.7692	Intermediate Similarity	NPC100267
0.7692	Intermediate Similarity	NPC475524
0.7692	Intermediate Similarity	NPC236217
0.7692	Intermediate Similarity	NPC221144
0.7686	Intermediate Similarity	NPC472004
0.7685	Intermediate Similarity	NPC469491
0.768	Intermediate Similarity	NPC236999
0.7679	Intermediate Similarity	NPC472754
0.7679	Intermediate Similarity	NPC78127
0.7679	Intermediate Similarity	NPC470972
0.7679	Intermediate Similarity	NPC471757
0.7672	Intermediate Similarity	NPC206595
0.7667	Intermediate Similarity	NPC257457
0.7667	Intermediate Similarity	NPC311554
0.7652	Intermediate Similarity	NPC472825
0.7642	Intermediate Similarity	NPC469789
0.7638	Intermediate Similarity	NPC155529
0.7636	Intermediate Similarity	NPC205143
0.7632	Intermediate Similarity	NPC475290
0.7632	Intermediate Similarity	NPC475802
0.7627	Intermediate Similarity	NPC46269
0.7627	Intermediate Similarity	NPC106395
0.7627	Intermediate Similarity	NPC194100
0.7623	Intermediate Similarity	NPC472001
0.7623	Intermediate Similarity	NPC67569
0.7619	Intermediate Similarity	NPC104382
0.7619	Intermediate Similarity	NPC221414
0.7615	Intermediate Similarity	NPC272050
0.7611	Intermediate Similarity	NPC23584
0.7611	Intermediate Similarity	NPC474775
0.7611	Intermediate Similarity	NPC280566
0.7611	Intermediate Similarity	NPC472755
0.7607	Intermediate Similarity	NPC470076
0.7603	Intermediate Similarity	NPC475775
0.7603	Intermediate Similarity	NPC476529
0.7603	Intermediate Similarity	NPC473203
0.7603	Intermediate Similarity	NPC9674
0.7603	Intermediate Similarity	NPC219656
0.7603	Intermediate Similarity	NPC19028
0.76	Intermediate Similarity	NPC470882
0.76	Intermediate Similarity	NPC287423
0.7589	Intermediate Similarity	NPC472753
0.7589	Intermediate Similarity	NPC150923
0.7586	Intermediate Similarity	NPC471934
0.7586	Intermediate Similarity	NPC475922
0.7586	Intermediate Similarity	NPC187876
0.7581	Intermediate Similarity	NPC8374
0.7581	Intermediate Similarity	NPC145238
0.7581	Intermediate Similarity	NPC81736
0.7581	Intermediate Similarity	NPC473255
0.7581	Intermediate Similarity	NPC172154
0.757	Intermediate Similarity	NPC3952
0.757	Intermediate Similarity	NPC177668

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 NPC101400 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1290
0.2-0.3	3677
0.3-0.4	2676
0.4-0.5	826
0.5-0.6	262
0.6-0.7	221
0.7-0.8	18
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
0.7905	Intermediate Similarity	NPD7838	Discovery
0.7736	Intermediate Similarity	NPD46	Approved
0.7736	Intermediate Similarity	NPD6698	Approved
0.7623	Intermediate Similarity	NPD7503	Approved
0.7565	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6319	Approved
0.7411	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD8297	Approved
0.7395	Intermediate Similarity	NPD6053	Discontinued
0.7373	Intermediate Similarity	NPD6371	Approved
0.735	Intermediate Similarity	NPD6686	Approved
0.7333	Intermediate Similarity	NPD4632	Approved
0.7295	Intermediate Similarity	NPD7115	Discovery
0.7257	Intermediate Similarity	NPD7638	Approved
0.7244	Intermediate Similarity	NPD7507	Approved
0.7231	Intermediate Similarity	NPD7260	Phase 2
0.7203	Intermediate Similarity	NPD6881	Approved
0.7203	Intermediate Similarity	NPD6899	Approved
0.72	Intermediate Similarity	NPD8033	Approved
0.7193	Intermediate Similarity	NPD7640	Approved
0.7193	Intermediate Similarity	NPD7639	Approved
0.7167	Intermediate Similarity	NPD6649	Approved
0.7167	Intermediate Similarity	NPD6650	Approved
0.7165	Intermediate Similarity	NPD7492	Approved
0.713	Intermediate Similarity	NPD5344	Discontinued
0.712	Intermediate Similarity	NPD6054	Approved
0.7119	Intermediate Similarity	NPD5697	Approved
0.7119	Intermediate Similarity	NPD6412	Phase 2
0.7109	Intermediate Similarity	NPD6616	Approved
0.7107	Intermediate Similarity	NPD6882	Approved
0.7097	Intermediate Similarity	NPD7327	Approved
0.7097	Intermediate Similarity	NPD7328	Approved
0.7087	Intermediate Similarity	NPD7604	Phase 2
0.7083	Intermediate Similarity	NPD7102	Approved
0.7083	Intermediate Similarity	NPD7290	Approved
0.7083	Intermediate Similarity	NPD6883	Approved
0.7077	Intermediate Similarity	NPD7319	Approved
0.7054	Intermediate Similarity	NPD7078	Approved
0.7043	Intermediate Similarity	NPD6648	Approved
0.704	Intermediate Similarity	NPD7516	Approved
0.7034	Intermediate Similarity	NPD7128	Approved
0.7034	Intermediate Similarity	NPD6402	Approved
0.7034	Intermediate Similarity	NPD5739	Approved
0.7034	Intermediate Similarity	NPD6675	Approved
0.7027	Intermediate Similarity	NPD7983	Approved
0.7025	Intermediate Similarity	NPD6847	Approved
0.7025	Intermediate Similarity	NPD8130	Phase 1
0.7025	Intermediate Similarity	NPD6617	Approved
0.7025	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6869	Approved
0.7018	Intermediate Similarity	NPD6083	Phase 2
0.7018	Intermediate Similarity	NPD6084	Phase 2
0.7016	Intermediate Similarity	NPD6009	Approved
0.7008	Intermediate Similarity	NPD6370	Approved
0.7	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD6013	Approved
0.7	Intermediate Similarity	NPD7736	Approved
0.7	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD6012	Approved
0.7	Intermediate Similarity	NPD6373	Approved
0.6984	Remote Similarity	NPD8377	Approved
0.6984	Remote Similarity	NPD8294	Approved
0.6972	Remote Similarity	NPD4250	Approved
0.6972	Remote Similarity	NPD4251	Approved
0.6952	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4821	Approved
0.6952	Remote Similarity	NPD4820	Approved
0.6952	Remote Similarity	NPD4819	Approved
0.6952	Remote Similarity	NPD4822	Approved
0.6942	Remote Similarity	NPD4634	Approved
0.6937	Remote Similarity	NPD5785	Approved
0.6929	Remote Similarity	NPD8335	Approved
0.6929	Remote Similarity	NPD8379	Approved
0.6929	Remote Similarity	NPD5983	Phase 2
0.6929	Remote Similarity	NPD8513	Phase 3
0.6929	Remote Similarity	NPD6016	Approved
0.6929	Remote Similarity	NPD8296	Approved
0.6929	Remote Similarity	NPD8516	Approved
0.6929	Remote Similarity	NPD8517	Approved
0.6929	Remote Similarity	NPD6015	Approved
0.6929	Remote Similarity	NPD8378	Approved
0.6929	Remote Similarity	NPD8515	Approved
0.6929	Remote Similarity	NPD8380	Approved
0.6917	Remote Similarity	NPD7320	Approved
0.6917	Remote Similarity	NPD6011	Approved
0.6881	Remote Similarity	NPD4249	Approved
0.6875	Remote Similarity	NPD5988	Approved
0.6875	Remote Similarity	NPD7637	Suspended
0.685	Remote Similarity	NPD6059	Approved
0.6846	Remote Similarity	NPD6336	Discontinued
0.6842	Remote Similarity	NPD5695	Phase 3
0.6833	Remote Similarity	NPD5701	Approved
0.6814	Remote Similarity	NPD5778	Approved
0.6814	Remote Similarity	NPD5779	Approved
0.681	Remote Similarity	NPD4225	Approved
0.6803	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD8293	Discontinued
0.6791	Remote Similarity	NPD6845	Suspended
0.678	Remote Similarity	NPD5211	Phase 2
0.6762	Remote Similarity	NPD4268	Approved
0.6762	Remote Similarity	NPD4271	Approved
0.6752	Remote Similarity	NPD5286	Approved
0.6752	Remote Similarity	NPD4696	Approved
0.6752	Remote Similarity	NPD5285	Approved
0.675	Remote Similarity	NPD6008	Approved
0.6726	Remote Similarity	NPD6411	Approved
0.6692	Remote Similarity	NPD7829	Approved
0.6692	Remote Similarity	NPD7830	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6641	Remote Similarity	NPD7101	Approved
0.6641	Remote Similarity	NPD7100	Approved
0.6639	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4633	Approved
0.6639	Remote Similarity	NPD7632	Discontinued
0.6639	Remote Similarity	NPD5226	Approved
0.6639	Remote Similarity	NPD5224	Approved
0.6639	Remote Similarity	NPD5225	Approved
0.6613	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5282	Discontinued
0.6594	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5174	Approved
0.6583	Remote Similarity	NPD5175	Approved
0.6581	Remote Similarity	NPD4755	Approved
0.6579	Remote Similarity	NPD5693	Phase 1
0.6579	Remote Similarity	NPD5281	Approved
0.6579	Remote Similarity	NPD5284	Approved
0.6579	Remote Similarity	NPD6050	Approved
0.6579	Remote Similarity	NPD5694	Approved
0.6562	Remote Similarity	NPD6335	Approved
0.6557	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5223	Approved
0.6552	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5210	Approved
0.6552	Remote Similarity	NPD4629	Approved
0.6549	Remote Similarity	NPD1695	Approved
0.6549	Remote Similarity	NPD6101	Approved
0.6549	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4753	Phase 2
0.6545	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6274	Approved
0.6514	Remote Similarity	NPD5209	Approved
0.6508	Remote Similarity	NPD8133	Approved
0.6504	Remote Similarity	NPD4729	Approved
0.6504	Remote Similarity	NPD4730	Approved
0.6491	Remote Similarity	NPD5692	Phase 3
0.6486	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5363	Approved
0.6484	Remote Similarity	NPD6317	Approved
0.6481	Remote Similarity	NPD5368	Approved
0.6471	Remote Similarity	NPD4700	Approved
0.6455	Remote Similarity	NPD5362	Discontinued
0.6455	Remote Similarity	NPD7154	Phase 3
0.6455	Remote Similarity	NPD6695	Phase 3
0.6439	Remote Similarity	NPD8328	Phase 3
0.6434	Remote Similarity	NPD6314	Approved
0.6434	Remote Similarity	NPD6313	Approved
0.6429	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD6409	Approved
0.6429	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD5330	Approved
0.6429	Remote Similarity	NPD7334	Approved
0.6429	Remote Similarity	NPD7146	Approved
0.6404	Remote Similarity	NPD6673	Approved
0.6404	Remote Similarity	NPD6051	Approved
0.6404	Remote Similarity	NPD6080	Approved
0.6404	Remote Similarity	NPD6904	Approved
0.64	Remote Similarity	NPD5251	Approved
0.64	Remote Similarity	NPD5247	Approved
0.64	Remote Similarity	NPD5250	Approved
0.64	Remote Similarity	NPD5249	Phase 3
0.64	Remote Similarity	NPD5248	Approved
0.6397	Remote Similarity	NPD5956	Approved
0.6385	Remote Similarity	NPD4522	Approved
0.6379	Remote Similarity	NPD6399	Phase 3
0.637	Remote Similarity	NPD6033	Approved
0.6356	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7839	Suspended
0.6343	Remote Similarity	NPD8273	Phase 1
0.6341	Remote Similarity	NPD4767	Approved
0.6341	Remote Similarity	NPD4768	Approved
0.6339	Remote Similarity	NPD1696	Phase 3
0.6339	Remote Similarity	NPD1694	Approved
0.6316	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5737	Approved
0.6316	Remote Similarity	NPD7642	Approved
0.6316	Remote Similarity	NPD6903	Approved
0.6316	Remote Similarity	NPD6672	Approved
0.6306	Remote Similarity	NPD5331	Approved
0.6306	Remote Similarity	NPD6110	Phase 1
0.6306	Remote Similarity	NPD5332	Approved
0.629	Remote Similarity	NPD6685	Approved
0.6288	Remote Similarity	NPD6909	Approved
0.6288	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD6908	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