NPASS Compound

Structure

NPC141970 OpenBabel07101719132D 57 60 0 0 1 0 0 0 0 0999 V2000 -2.5112 -0.6872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2584 7.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9904 6.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9037 0.8208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6751 1.2256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5803 -0.3219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2584 6.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9904 -1.8468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4021 -1.7581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9186 4.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0526 4.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9186 3.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5787 -1.7581 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 -0.7985 -0.9454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1866 4.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0526 2.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1148 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4299 -1.0953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3205 2.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8484 -0.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4545 3.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9808 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3480 1.6123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1244 5.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9148 0.9698 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3098 2.1564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1866 3.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5509 -1.0953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1324 -0.5801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8564 1.9475 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9363 0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5885 2.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1091 1.6123 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1244 2.9475 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6975 1.5236 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8564 2.9475 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9904 3.4475 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2618 1.1472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1244 4.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1244 1.9475 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0445 0.5933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9333 2.9383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3328 -1.7188 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9113 0.8158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5885 1.9475 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2562 2.5432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2584 3.4475 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2584 4.4475 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7190 1.1472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5439 0.5046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3209 2.3055 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 1.9904 1.4475 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7225 3.4475 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9904 4.4475 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6328 1.6123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 25 1 0 0 0 0 5 27 1 0 0 0 0 6 15 1 0 0 0 0 7 25 2 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 16 1 0 0 0 0 12 17 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 16 28 2 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 22 2 0 0 0 0 20 28 1 0 0 0 0 21 23 1 0 0 0 0 21 29 1 0 0 0 0 22 33 1 0 0 0 0 23 32 1 0 0 0 0 24 50 1 0 0 0 0 25 40 1 0 0 0 0 26 4 1 6 0 0 0 26 36 1 0 0 0 0 26 51 1 0 0 0 0 27 43 2 0 0 0 0 27 52 1 0 0 0 0 29 44 2 0 0 0 0 30 15 1 6 0 0 0 30 53 1 0 0 0 0 31 24 1 1 0 0 0 31 37 1 0 0 0 0 31 54 1 0 0 0 0 32 45 2 0 0 0 0 32 50 1 0 0 0 0 33 46 2 0 0 0 0 33 55 1 0 0 0 0 34 36 1 0 0 0 0 34 39 1 0 0 0 0 34 47 1 6 0 0 0 35 38 1 0 0 0 0 35 41 1 0 0 0 0 35 48 1 6 0 0 0 36 52 1 6 0 0 0 37 38 1 0 0 0 0 37 55 1 6 0 0 0 38 56 1 1 0 0 0 39 42 1 0 0 0 0 39 57 1 1 0 0 0 40 49 2 0 0 0 0 40 56 1 0 0 0 0 41 54 1 1 0 0 0 41 57 1 0 0 0 0 42 51 1 6 0 0 0 42 53 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	802.38
Volume:	806.251
LogP:	4.201
LogD:	2.972
LogS:	-4.728
# Rotatable Bonds:	11
TPSA:	199.65
# H-Bond Aceptor:	15
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.212
Synthetic Accessibility Score:	6.519
Fsp3:	0.643
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:	-5.059
MDCK Permeability:	7.597146759508178e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.112
20% Bioavailability (F20%):	0.05
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	92.7441635131836%
Volume Distribution (VD):	1.617
Pgp-substrate:	3.5956649780273438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.335
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.848
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.668
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.957
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	1.825
Half-life (T1/2):	0.773

ADMET: Toxicity

hERG Blockers:	0.722
Human Hepatotoxicity (H-HT):	0.991
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.238
Rat Oral Acute Toxicity:	0.625
Maximum Recommended Daily Dose:	0.047
Skin Sensitization:	0.869
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.057

Download Data

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

Natural Product: NPC141970

Natural Product ID:	NPC141970
*Common Name:**	Ipomoeassin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UIMJTDXGFNDFRJ-ZOHZRQPWSA-N
Standard InCHI:	InChI=1S/C42H58O15/c1-6-15-30-19-14-9-8-13-18-29(44)21-23-32(45)50-24-31-37(55-33(46)22-20-28-16-11-10-12-17-28)38(56-40(49)25(3)7-2)35(48)41(54-31)57-39-34(47)36(52-27(5)43)26(4)51-42(39)53-30/h7,10-12,16-17,20,22,26,30-31,34-39,41-42,47-48H,6,8-9,13-15,18-19,21,23-24H2,1-5H3/b22-20+,25-7+/t26-,30+,31-,34+,35-,36+,37-,38-,39-,41+,42+/m1/s1
SMILES:	CCC[C@H]1CCCCCCC(=O)CCC(=O)OC[C@H]2O[C@@H](O[C@H]3[C@H](O1)O[C@H](C)[C@@H]([C@@H]3O)OC(=O)C)[C@H](O)[C@H]([C@@H]2OC(=O)/C=C/c1ccccc1)OC(=O)/C(=C/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506305
PubChem CID:	11308828
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

*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
NPO17901	Ipomoea squamosa	Species	Convolvulaceae	Eukaryota	leaves	Suriname rainforest	n.a.	PMID[15844934]
NPO17901	Ipomoea squamosa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	8

Activity Type	# Activity
Cell Line	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	500.0	nM	PMID[507004]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	64.0	nM	PMID[507005]
NPT1460	Cell Line	L929	Mus musculus	IC50	=	77.8	nM	PMID[507005]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	500.0	nM	PMID[507005]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	20.2	nM	PMID[507005]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	46.1	nM	PMID[507005]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	42.6	nM	PMID[507005]
NPT2	Others	Unspecified		IC50	=	108.9	nM	PMID[507005]

☑ 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 NPC141970 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	238
0.1-0.2	864
0.2-0.3	2133
0.3-0.4	5725
0.4-0.5	10215
0.5-0.6	17083
0.6-0.7	5512
0.7-0.8	859
0.8-0.85	34
0.85-0.9	25
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC140561
0.9583	High Similarity	NPC231627
0.9504	High Similarity	NPC226101
0.9504	High Similarity	NPC237182
0.9483	High Similarity	NPC476096
0.9333	High Similarity	NPC162925
0.9333	High Similarity	NPC87153
0.9256	High Similarity	NPC28069
0.9256	High Similarity	NPC77651
0.918	High Similarity	NPC198918
0.918	High Similarity	NPC204214
0.918	High Similarity	NPC10121
0.918	High Similarity	NPC92283
0.918	High Similarity	NPC10883
0.918	High Similarity	NPC63404
0.918	High Similarity	NPC35338
0.918	High Similarity	NPC124878
0.918	High Similarity	NPC231888
0.918	High Similarity	NPC290276
0.9106	High Similarity	NPC471025
0.9091	High Similarity	NPC473881
0.9032	High Similarity	NPC471024
0.8957	High Similarity	NPC470825
0.8871	High Similarity	NPC471026
0.8871	High Similarity	NPC147032
0.871	High Similarity	NPC57607
0.8696	High Similarity	NPC184633
0.8651	High Similarity	NPC148026
0.8644	High Similarity	NPC474641
0.8571	High Similarity	NPC114096
0.856	High Similarity	NPC244454
0.8516	High Similarity	NPC11025
0.845	Intermediate Similarity	NPC289415
0.845	Intermediate Similarity	NPC319995
0.8438	Intermediate Similarity	NPC301857
0.8417	Intermediate Similarity	NPC29607
0.839	Intermediate Similarity	NPC43584
0.8308	Intermediate Similarity	NPC17567
0.8261	Intermediate Similarity	NPC469527
0.8258	Intermediate Similarity	NPC322503
0.8258	Intermediate Similarity	NPC470143
0.8248	Intermediate Similarity	NPC111466
0.824	Intermediate Similarity	NPC229600
0.8231	Intermediate Similarity	NPC27712
0.8189	Intermediate Similarity	NPC138798
0.8188	Intermediate Similarity	NPC40085
0.8188	Intermediate Similarity	NPC264270
0.8175	Intermediate Similarity	NPC284957
0.812	Intermediate Similarity	NPC38420
0.812	Intermediate Similarity	NPC136608
0.8092	Intermediate Similarity	NPC473443
0.8083	Intermediate Similarity	NPC30563
0.8015	Intermediate Similarity	NPC475195
0.8015	Intermediate Similarity	NPC225103
0.8	Intermediate Similarity	NPC276061
0.8	Intermediate Similarity	NPC474148
0.7984	Intermediate Similarity	NPC145287
0.797	Intermediate Similarity	NPC235294
0.797	Intermediate Similarity	NPC46137
0.797	Intermediate Similarity	NPC80599
0.7955	Intermediate Similarity	NPC472388
0.7941	Intermediate Similarity	NPC471345
0.7939	Intermediate Similarity	NPC106677
0.7926	Intermediate Similarity	NPC169398
0.791	Intermediate Similarity	NPC159811
0.7883	Intermediate Similarity	NPC65262
0.7883	Intermediate Similarity	NPC469364
0.7883	Intermediate Similarity	NPC101686
0.7868	Intermediate Similarity	NPC263829
0.7863	Intermediate Similarity	NPC276047
0.7863	Intermediate Similarity	NPC267733
0.7846	Intermediate Similarity	NPC317163
0.7842	Intermediate Similarity	NPC475513
0.7842	Intermediate Similarity	NPC473755
0.7836	Intermediate Similarity	NPC209851
0.7836	Intermediate Similarity	NPC246869
0.7836	Intermediate Similarity	NPC138777
0.7836	Intermediate Similarity	NPC281798
0.7836	Intermediate Similarity	NPC225384
0.7826	Intermediate Similarity	NPC324262
0.7826	Intermediate Similarity	NPC62800
0.7817	Intermediate Similarity	NPC212808
0.7808	Intermediate Similarity	NPC87403
0.7803	Intermediate Similarity	NPC288416
0.7801	Intermediate Similarity	NPC471028
0.7801	Intermediate Similarity	NPC202391
0.7801	Intermediate Similarity	NPC296659
0.7786	Intermediate Similarity	NPC148080
0.7786	Intermediate Similarity	NPC469623
0.7778	Intermediate Similarity	NPC329657
0.7761	Intermediate Similarity	NPC305162
0.7761	Intermediate Similarity	NPC475478
0.7755	Intermediate Similarity	NPC477735
0.773	Intermediate Similarity	NPC293154
0.773	Intermediate Similarity	NPC478250
0.7727	Intermediate Similarity	NPC471157
0.7727	Intermediate Similarity	NPC252114
0.7721	Intermediate Similarity	NPC114116
0.7714	Intermediate Similarity	NPC80098
0.7714	Intermediate Similarity	NPC79908
0.7704	Intermediate Similarity	NPC478255
0.7704	Intermediate Similarity	NPC475569
0.7704	Intermediate Similarity	NPC471880
0.7703	Intermediate Similarity	NPC477736
0.7698	Intermediate Similarity	NPC31745
0.7698	Intermediate Similarity	NPC220936
0.7692	Intermediate Similarity	NPC52097
0.7686	Intermediate Similarity	NPC20485
0.7671	Intermediate Similarity	NPC69425
0.7669	Intermediate Similarity	NPC45224
0.7669	Intermediate Similarity	NPC471881
0.7669	Intermediate Similarity	NPC195224
0.7669	Intermediate Similarity	NPC156692
0.7669	Intermediate Similarity	NPC471882
0.7669	Intermediate Similarity	NPC103533
0.7669	Intermediate Similarity	NPC175333
0.7669	Intermediate Similarity	NPC173150
0.7669	Intermediate Similarity	NPC35288
0.7669	Intermediate Similarity	NPC230331
0.7667	Intermediate Similarity	NPC152384
0.7667	Intermediate Similarity	NPC37714
0.7664	Intermediate Similarity	NPC34456
0.7655	Intermediate Similarity	NPC96599
0.7655	Intermediate Similarity	NPC478242
0.7655	Intermediate Similarity	NPC469415
0.7652	Intermediate Similarity	NPC470818
0.7652	Intermediate Similarity	NPC470816
0.7652	Intermediate Similarity	NPC126991
0.7652	Intermediate Similarity	NPC79608
0.7652	Intermediate Similarity	NPC123704
0.7652	Intermediate Similarity	NPC476033
0.7652	Intermediate Similarity	NPC83218
0.7643	Intermediate Similarity	NPC77493
0.7642	Intermediate Similarity	NPC264784
0.7638	Intermediate Similarity	NPC216605
0.7638	Intermediate Similarity	NPC266389
0.7638	Intermediate Similarity	NPC122245
0.7634	Intermediate Similarity	NPC469742
0.763	Intermediate Similarity	NPC469705
0.763	Intermediate Similarity	NPC470122
0.763	Intermediate Similarity	NPC17968
0.7622	Intermediate Similarity	NPC477737
0.7619	Intermediate Similarity	NPC469456
0.7619	Intermediate Similarity	NPC106818
0.7615	Intermediate Similarity	NPC475328
0.7615	Intermediate Similarity	NPC11724
0.7612	Intermediate Similarity	NPC225307
0.7607	Intermediate Similarity	NPC262826
0.7606	Intermediate Similarity	NPC152796
0.7606	Intermediate Similarity	NPC475213
0.7606	Intermediate Similarity	NPC242756
0.7606	Intermediate Similarity	NPC469367
0.7603	Intermediate Similarity	NPC35097
0.7603	Intermediate Similarity	NPC117346
0.7603	Intermediate Similarity	NPC240592
0.76	Intermediate Similarity	NPC172525
0.76	Intermediate Similarity	NPC474363
0.7594	Intermediate Similarity	NPC61181
0.7594	Intermediate Similarity	NPC473423
0.7589	Intermediate Similarity	NPC47471
0.7589	Intermediate Similarity	NPC476377
0.7586	Intermediate Similarity	NPC28776
0.7586	Intermediate Similarity	NPC222102
0.7586	Intermediate Similarity	NPC303429
0.7586	Intermediate Similarity	NPC120728
0.7586	Intermediate Similarity	NPC473138
0.7586	Intermediate Similarity	NPC469448
0.7584	Intermediate Similarity	NPC477467
0.7583	Intermediate Similarity	NPC47286
0.7574	Intermediate Similarity	NPC475493
0.7571	Intermediate Similarity	NPC472350
0.7571	Intermediate Similarity	NPC476383
0.7571	Intermediate Similarity	NPC473440
0.7571	Intermediate Similarity	NPC197316
0.7571	Intermediate Similarity	NPC89105
0.7571	Intermediate Similarity	NPC81515
0.7571	Intermediate Similarity	NPC68092
0.7571	Intermediate Similarity	NPC64141
0.7569	Intermediate Similarity	NPC473147
0.7569	Intermediate Similarity	NPC474268
0.7569	Intermediate Similarity	NPC143246
0.7569	Intermediate Similarity	NPC291153
0.7569	Intermediate Similarity	NPC475539
0.7569	Intermediate Similarity	NPC119773
0.7556	Intermediate Similarity	NPC253595
0.7556	Intermediate Similarity	NPC469549
0.7554	Intermediate Similarity	NPC472132
0.7552	Intermediate Similarity	NPC194938
0.7551	Intermediate Similarity	NPC475379
0.755	Intermediate Similarity	NPC165234
0.755	Intermediate Similarity	NPC475536
0.7538	Intermediate Similarity	NPC476872
0.7535	Intermediate Similarity	NPC245219
0.7535	Intermediate Similarity	NPC65833
0.7535	Intermediate Similarity	NPC296643
0.7535	Intermediate Similarity	NPC31081
0.7518	Intermediate Similarity	NPC472248
0.7518	Intermediate Similarity	NPC15850
0.7518	Intermediate Similarity	NPC475530
0.7518	Intermediate Similarity	NPC471095

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 NPC141970 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	639
0.2-0.3	1461
0.3-0.4	3107
0.4-0.5	2441
0.5-0.6	1057
0.6-0.7	231
0.7-0.8	8
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7266	Discontinued
0.7569	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6647	Phase 2
0.728	Intermediate Similarity	NPD2067	Discontinued
0.725	Intermediate Similarity	NPD7798	Approved
0.7236	Intermediate Similarity	NPD5048	Discontinued
0.7167	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD969	Suspended
0.7068	Intermediate Similarity	NPD5126	Approved
0.7068	Intermediate Similarity	NPD5125	Phase 3
0.7063	Intermediate Similarity	NPD2182	Approved
0.7059	Intermediate Similarity	NPD8455	Phase 2
0.704	Intermediate Similarity	NPD6685	Approved
0.7016	Intermediate Similarity	NPD5909	Discontinued
0.6984	Remote Similarity	NPD6686	Approved
0.6975	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6010	Discontinued
0.6892	Remote Similarity	NPD6190	Approved
0.687	Remote Similarity	NPD2629	Approved
0.6852	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD8312	Approved
0.6848	Remote Similarity	NPD8313	Approved
0.6835	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5765	Approved
0.68	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7799	Discontinued
0.6769	Remote Similarity	NPD6912	Phase 3
0.6748	Remote Similarity	NPD9495	Approved
0.6748	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD164	Approved
0.6742	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7685	Pre-registration
0.6715	Remote Similarity	NPD1091	Approved
0.6711	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD2066	Phase 3
0.6692	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7054	Approved
0.6644	Remote Similarity	NPD7097	Phase 1
0.6639	Remote Similarity	NPD689	Discontinued
0.6627	Remote Similarity	NPD8368	Discontinued
0.6618	Remote Similarity	NPD8516	Approved
0.6618	Remote Similarity	NPD8515	Approved
0.6618	Remote Similarity	NPD8517	Approved
0.6618	Remote Similarity	NPD8513	Phase 3
0.6606	Remote Similarity	NPD7472	Approved
0.6606	Remote Similarity	NPD7074	Phase 3
0.66	Remote Similarity	NPD4628	Phase 3
0.6597	Remote Similarity	NPD6233	Phase 2
0.6587	Remote Similarity	NPD1932	Approved
0.6587	Remote Similarity	NPD7808	Phase 3
0.6585	Remote Similarity	NPD7228	Approved
0.6583	Remote Similarity	NPD46	Approved
0.6583	Remote Similarity	NPD6698	Approved
0.6567	Remote Similarity	NPD4198	Discontinued
0.6565	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.656	Remote Similarity	NPD1238	Approved
0.6558	Remote Similarity	NPD5403	Approved
0.6547	Remote Similarity	NPD6637	Approved
0.6544	Remote Similarity	NPD9545	Approved
0.6538	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD5401	Approved
0.6531	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6559	Discontinued
0.6527	Remote Similarity	NPD7251	Discontinued
0.6522	Remote Similarity	NPD7829	Approved
0.6522	Remote Similarity	NPD7830	Approved
0.6519	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD1653	Approved
0.651	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD8407	Phase 2
0.65	Remote Similarity	NPD5346	Phase 2
0.65	Remote Similarity	NPD7075	Discontinued
0.65	Remote Similarity	NPD5347	Phase 2
0.6488	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD3818	Discontinued
0.6484	Remote Similarity	NPD1237	Approved
0.6483	Remote Similarity	NPD7961	Discontinued
0.6478	Remote Similarity	NPD5402	Approved
0.6471	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1282	Approved
0.6471	Remote Similarity	NPD4793	Discontinued
0.6467	Remote Similarity	NPD6797	Phase 2
0.6466	Remote Similarity	NPD6858	Approved
0.6466	Remote Similarity	NPD7094	Approved
0.6456	Remote Similarity	NPD37	Approved
0.6446	Remote Similarity	NPD3673	Approved
0.6446	Remote Similarity	NPD7838	Discovery
0.6446	Remote Similarity	NPD3672	Approved
0.6438	Remote Similarity	NPD4966	Approved
0.6438	Remote Similarity	NPD4967	Phase 2
0.6438	Remote Similarity	NPD4965	Approved
0.6433	Remote Similarity	NPD4380	Phase 2
0.6429	Remote Similarity	NPD7240	Approved
0.6414	Remote Similarity	NPD6798	Discontinued
0.6414	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD2329	Discontinued
0.6408	Remote Similarity	NPD2625	Approved
0.6408	Remote Similarity	NPD2628	Approved
0.6408	Remote Similarity	NPD2160	Approved
0.6408	Remote Similarity	NPD2627	Approved
0.6408	Remote Similarity	NPD2626	Approved
0.6408	Remote Similarity	NPD2159	Approved
0.6406	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD1929	Approved
0.6406	Remote Similarity	NPD1930	Approved
0.6405	Remote Similarity	NPD7236	Approved
0.6395	Remote Similarity	NPD230	Phase 1
0.6389	Remote Similarity	NPD2613	Approved
0.6384	Remote Similarity	NPD7700	Phase 2
0.6384	Remote Similarity	NPD7699	Phase 2
0.6382	Remote Similarity	NPD8166	Discontinued
0.6382	Remote Similarity	NPD2575	Approved
0.6379	Remote Similarity	NPD226	Approved
0.6364	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6085	Phase 2
0.6364	Remote Similarity	NPD1317	Discontinued
0.6364	Remote Similarity	NPD6799	Approved
0.6364	Remote Similarity	NPD5647	Approved
0.6358	Remote Similarity	NPD6234	Discontinued
0.6357	Remote Similarity	NPD4806	Approved
0.6357	Remote Similarity	NPD4807	Approved
0.6354	Remote Similarity	NPD8320	Phase 1
0.6354	Remote Similarity	NPD8319	Approved
0.6352	Remote Similarity	NPD6801	Discontinued
0.6349	Remote Similarity	NPD5926	Approved
0.6346	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD5306	Approved
0.6331	Remote Similarity	NPD5305	Approved
0.632	Remote Similarity	NPD1989	Approved
0.6316	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1652	Phase 2
0.6312	Remote Similarity	NPD7819	Suspended
0.6306	Remote Similarity	NPD7239	Suspended
0.6304	Remote Similarity	NPD7741	Discontinued
0.6301	Remote Similarity	NPD3764	Approved
0.6287	Remote Similarity	NPD3751	Discontinued
0.6286	Remote Similarity	NPD4106	Approved
0.6286	Remote Similarity	NPD4135	Approved
0.6286	Remote Similarity	NPD4136	Approved
0.6284	Remote Similarity	NPD6355	Discontinued
0.6284	Remote Similarity	NPD1933	Approved
0.6277	Remote Similarity	NPD7641	Discontinued
0.6276	Remote Similarity	NPD5203	Approved
0.6276	Remote Similarity	NPD5201	Approved
0.6276	Remote Similarity	NPD4617	Approved
0.6276	Remote Similarity	NPD6832	Phase 2
0.6276	Remote Similarity	NPD4620	Approved
0.6272	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD9491	Approved
0.6267	Remote Similarity	NPD7033	Discontinued
0.6266	Remote Similarity	NPD7458	Discontinued
0.6266	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8360	Approved
0.6264	Remote Similarity	NPD8361	Approved
0.6264	Remote Similarity	NPD8435	Approved
0.626	Remote Similarity	NPD7983	Approved
0.6259	Remote Similarity	NPD4745	Approved
0.6259	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD2574	Discontinued
0.6259	Remote Similarity	NPD3089	Approved
0.6259	Remote Similarity	NPD2573	Approved
0.6259	Remote Similarity	NPD3615	Approved
0.6259	Remote Similarity	NPD3616	Approved
0.6259	Remote Similarity	NPD2571	Approved
0.6259	Remote Similarity	NPD3087	Approved
0.6259	Remote Similarity	NPD3090	Approved
0.6259	Remote Similarity	NPD4746	Phase 3
0.6259	Remote Similarity	NPD3614	Approved
0.6259	Remote Similarity	NPD2570	Approved
0.6259	Remote Similarity	NPD3088	Approved
0.6259	Remote Similarity	NPD4062	Phase 3
0.6259	Remote Similarity	NPD2566	Approved
0.6243	Remote Similarity	NPD8150	Discontinued
0.6243	Remote Similarity	NPD8434	Phase 2
0.6242	Remote Similarity	NPD6653	Approved
0.6241	Remote Similarity	NPD6287	Discontinued
0.624	Remote Similarity	NPD1693	Approved
0.6233	Remote Similarity	NPD7008	Discontinued
0.623	Remote Similarity	NPD800	Approved
0.6224	Remote Similarity	NPD5667	Approved
0.6216	Remote Similarity	NPD5119	Approved
0.6216	Remote Similarity	NPD5121	Approved
0.6216	Remote Similarity	NPD5120	Approved
0.6215	Remote Similarity	NPD6534	Approved
0.6215	Remote Similarity	NPD6535	Approved
0.6209	Remote Similarity	NPD7435	Discontinued
0.6197	Remote Similarity	NPD8451	Approved
0.619	Remote Similarity	NPD3268	Approved
0.619	Remote Similarity	NPD2313	Discontinued
0.6188	Remote Similarity	NPD7411	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