NPASS Compound

Structure

CID118405 OpenBabel06191715472D 34 36 0 0 1 0 0 0 0 0999 V2000 3.6709 6.0170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8879 -1.7870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5769 -0.2355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5251 0.7897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9279 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9279 0.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1064 5.1915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5391 4.2899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9747 3.4645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4073 2.5629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7456 2.7162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6552 2.3007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6552 -0.3818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8255 -0.5644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3403 3.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7456 -0.7972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6174 0.0462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7210 0.1953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7557 2.5738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1958 1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1958 0.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2817 0.9595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8429 1.7374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2813 0.9880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7557 -0.6549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0619 0.9595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9204 4.2981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8338 -0.7983 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2755 0.8359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3403 -1.5645 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8458 1.8135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8041 0.5945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 17 1 0 0 0 0 4 19 1 0 0 0 0 5 27 1 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 13 17 2 0 0 0 0 14 20 2 0 0 0 0 14 23 1 0 0 0 0 15 18 1 0 0 0 0 15 28 1 0 0 0 0 16 20 1 0 0 0 0 16 29 1 0 0 0 0 17 26 1 0 0 0 0 18 3 1 1 0 0 0 18 25 1 0 0 0 0 19 30 2 0 0 0 0 19 34 1 0 0 0 0 21 12 1 1 0 0 0 21 22 1 0 0 0 0 21 27 1 0 0 0 0 22 13 1 1 0 0 0 22 27 1 0 0 0 0 23 25 1 0 0 0 0 23 28 1 1 0 0 0 24 31 2 0 0 0 0 24 33 1 0 0 0 0 25 33 1 1 0 0 0 26 28 1 0 0 0 0 26 32 2 0 0 0 0 28 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.3
Volume:	506.734
LogP:	4.581
LogD:	4.258
LogS:	-4.73
# Rotatable Bonds:	9
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.319
Synthetic Accessibility Score:	5.153
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.793
MDCK Permeability:	2.1966850908938795e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.868
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.972
Plasma Protein Binding (PPB):	79.15950775146484%
Volume Distribution (VD):	0.726
Pgp-substrate:	23.577783584594727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.391
CYP2C19-substrate:	0.242
CYP2C9-inhibitor:	0.765
CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.928
CYP3A4-substrate:	0.439

ADMET: Excretion

Clearance (CL):	8.145
Half-life (T1/2):	0.65

ADMET: Toxicity

hERG Blockers:	0.43
Human Hepatotoxicity (H-HT):	0.798
Drug-inuced Liver Injury (DILI):	0.599
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.597
Maximum Recommended Daily Dose:	0.854
Skin Sensitization:	0.857
Carcinogencity:	0.209
Eye Corrosion:	0.004
Eye Irritation:	0.023
Respiratory Toxicity:	0.781

Download Data

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

Natural Product: NPC118405

Natural Product ID:	NPC118405
*Common Name:**	QWEBGLOUXCMOMA-WDXCJRAPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QWEBGLOUXCMOMA-WDXCJRAPSA-N
Standard InCHI:	InChI=1S/C28H42O6/c1-7-8-9-10-24(31)33-25-18(3)15-28(34-19(4)30)23(25)14-20(16-29)11-12-21-22(27(21,5)6)13-17(2)26(28)32/h13-14,18,21-23,25,29H,7-12,15-16H2,1-6H3/b17-13+,20-14-/t18-,21-,22+,23-,25-,28+/m0/s1
SMILES:	CCCCCC(=O)O[C@H]1[C@@H](C)C[C@]2([C@H]1/C=C(CO)/CC[C@H]1[C@@H](/C=C(/C2=O)C)C1(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518541
PubChem CID:	11754671
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542364]
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15165157]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	bark	n.a.	n.a.	PMID[21627109]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21627109]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30817151]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10479	Ophiocoma echinata	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3940	Erioderma chilense	Species	Pannariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10959	Kalanchoe marmorata	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1000	Thymus transcaucasicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10833	Heteromma simplicifolium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5571	Jacobaea arnautorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4494	Ecbolium linneanum	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8283	Pseudophegopteris subaurita	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10733	Plantago uniflora	Species	Plantaginaceae	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
Kd	1
Others	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	78.5	%	PMID[449511]
NPT2	Others	Unspecified		Kd	=	16900.0	nM	PMID[449511]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	95.0	%	PMID[449511]

☑ 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 NPC118405 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	237
0.1-0.2	1415
0.2-0.3	5674
0.3-0.4	12488
0.4-0.5	10634
0.5-0.6	6683
0.6-0.7	4270
0.7-0.8	1243
0.8-0.85	34
0.85-0.9	6
0.9-0.95	7
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9574	High Similarity	NPC87090
0.9479	High Similarity	NPC477356
0.9271	High Similarity	NPC477355
0.9149	High Similarity	NPC202824
0.9149	High Similarity	NPC125180
0.9149	High Similarity	NPC477361
0.9062	High Similarity	NPC477354
0.8624	High Similarity	NPC477092
0.8611	High Similarity	NPC475305
0.8532	High Similarity	NPC475401
0.8333	Intermediate Similarity	NPC477950
0.8318	Intermediate Similarity	NPC475495
0.8317	Intermediate Similarity	NPC222011
0.8269	Intermediate Similarity	NPC235889
0.8241	Intermediate Similarity	NPC477093
0.8241	Intermediate Similarity	NPC475277
0.8241	Intermediate Similarity	NPC473522
0.8218	Intermediate Similarity	NPC69385
0.819	Intermediate Similarity	NPC181265
0.8182	Intermediate Similarity	NPC109414
0.8148	Intermediate Similarity	NPC231589
0.8148	Intermediate Similarity	NPC214797
0.8148	Intermediate Similarity	NPC118860
0.8131	Intermediate Similarity	NPC241927
0.8131	Intermediate Similarity	NPC258543
0.8113	Intermediate Similarity	NPC470192
0.8095	Intermediate Similarity	NPC309190
0.8081	Intermediate Similarity	NPC221282
0.8077	Intermediate Similarity	NPC87351
0.8073	Intermediate Similarity	NPC475524
0.8073	Intermediate Similarity	NPC170487
0.8073	Intermediate Similarity	NPC100267
0.8073	Intermediate Similarity	NPC221144
0.8058	Intermediate Similarity	NPC476274
0.8041	Intermediate Similarity	NPC471738
0.8018	Intermediate Similarity	NPC148458
0.8	Intermediate Similarity	NPC472755
0.8	Intermediate Similarity	NPC236390
0.8	Intermediate Similarity	NPC311612
0.8	Intermediate Similarity	NPC111323
0.7982	Intermediate Similarity	NPC158523
0.7982	Intermediate Similarity	NPC475937
0.7981	Intermediate Similarity	NPC476240
0.7981	Intermediate Similarity	NPC224720
0.7981	Intermediate Similarity	NPC476223
0.798	Intermediate Similarity	NPC469368
0.7963	Intermediate Similarity	NPC474901
0.7963	Intermediate Similarity	NPC475941
0.7961	Intermediate Similarity	NPC470188
0.7961	Intermediate Similarity	NPC197386
0.7946	Intermediate Similarity	NPC471854
0.7944	Intermediate Similarity	NPC44063
0.7921	Intermediate Similarity	NPC90453
0.7909	Intermediate Similarity	NPC71348
0.7905	Intermediate Similarity	NPC195290
0.7905	Intermediate Similarity	NPC119601
0.7905	Intermediate Similarity	NPC308351
0.7905	Intermediate Similarity	NPC271266
0.7905	Intermediate Similarity	NPC204450
0.7905	Intermediate Similarity	NPC105725
0.7905	Intermediate Similarity	NPC308726
0.7905	Intermediate Similarity	NPC471757
0.7905	Intermediate Similarity	NPC78127
0.79	Intermediate Similarity	NPC219874
0.789	Intermediate Similarity	NPC153036
0.789	Intermediate Similarity	NPC257240
0.787	Intermediate Similarity	NPC117604
0.7864	Intermediate Similarity	NPC161493
0.7857	Intermediate Similarity	NPC270958
0.785	Intermediate Similarity	NPC314244
0.785	Intermediate Similarity	NPC473488
0.785	Intermediate Similarity	NPC475661
0.7843	Intermediate Similarity	NPC470974
0.7843	Intermediate Similarity	NPC470978
0.7843	Intermediate Similarity	NPC472469
0.7838	Intermediate Similarity	NPC71889
0.7838	Intermediate Similarity	NPC202889
0.7833	Intermediate Similarity	NPC477370
0.7818	Intermediate Similarity	NPC43775
0.781	Intermediate Similarity	NPC163372
0.781	Intermediate Similarity	NPC185141
0.781	Intermediate Similarity	NPC110443
0.781	Intermediate Similarity	NPC472753
0.781	Intermediate Similarity	NPC46998
0.781	Intermediate Similarity	NPC128733
0.781	Intermediate Similarity	NPC171759
0.781	Intermediate Similarity	NPC302537
0.781	Intermediate Similarity	NPC133907
0.7798	Intermediate Similarity	NPC47951
0.7798	Intermediate Similarity	NPC304495
0.7798	Intermediate Similarity	NPC471400
0.7798	Intermediate Similarity	NPC2766
0.7789	Intermediate Similarity	NPC88735
0.7788	Intermediate Similarity	NPC109556
0.7788	Intermediate Similarity	NPC239273
0.7788	Intermediate Similarity	NPC141191
0.7788	Intermediate Similarity	NPC221615
0.7778	Intermediate Similarity	NPC185
0.7778	Intermediate Similarity	NPC475294
0.7768	Intermediate Similarity	NPC474872
0.7767	Intermediate Similarity	NPC24956
0.7767	Intermediate Similarity	NPC184065
0.7767	Intermediate Similarity	NPC213078
0.7767	Intermediate Similarity	NPC18019
0.7757	Intermediate Similarity	NPC137657
0.7757	Intermediate Similarity	NPC310586
0.775	Intermediate Similarity	NPC477365
0.7748	Intermediate Similarity	NPC138757
0.7748	Intermediate Similarity	NPC123855
0.7748	Intermediate Similarity	NPC475970
0.7748	Intermediate Similarity	NPC76550
0.7745	Intermediate Similarity	NPC469632
0.7736	Intermediate Similarity	NPC15396
0.7736	Intermediate Similarity	NPC472754
0.7736	Intermediate Similarity	NPC136289
0.7736	Intermediate Similarity	NPC49393
0.7736	Intermediate Similarity	NPC470840
0.7736	Intermediate Similarity	NPC56498
0.7727	Intermediate Similarity	NPC41551
0.7727	Intermediate Similarity	NPC50223
0.7727	Intermediate Similarity	NPC477103
0.7719	Intermediate Similarity	NPC311554
0.7719	Intermediate Similarity	NPC472397
0.7719	Intermediate Similarity	NPC471125
0.7719	Intermediate Similarity	NPC118638
0.7719	Intermediate Similarity	NPC171905
0.7719	Intermediate Similarity	NPC472758
0.7719	Intermediate Similarity	NPC257457
0.7714	Intermediate Similarity	NPC241221
0.7714	Intermediate Similarity	NPC205899
0.7706	Intermediate Similarity	NPC470269
0.77	Intermediate Similarity	NPC476388
0.77	Intermediate Similarity	NPC170775
0.77	Intermediate Similarity	NPC232747
0.77	Intermediate Similarity	NPC212664
0.77	Intermediate Similarity	NPC477215
0.7692	Intermediate Similarity	NPC477949
0.7692	Intermediate Similarity	NPC169205
0.7692	Intermediate Similarity	NPC18319
0.7692	Intermediate Similarity	NPC107243
0.7685	Intermediate Similarity	NPC472751
0.7685	Intermediate Similarity	NPC179891
0.7685	Intermediate Similarity	NPC470267
0.7685	Intermediate Similarity	NPC472749
0.7685	Intermediate Similarity	NPC243998
0.7685	Intermediate Similarity	NPC54737
0.7679	Intermediate Similarity	NPC472929
0.7679	Intermediate Similarity	NPC46269
0.7679	Intermediate Similarity	NPC106395
0.7677	Intermediate Similarity	NPC237540
0.7672	Intermediate Similarity	NPC472401
0.767	Intermediate Similarity	NPC163228
0.767	Intermediate Similarity	NPC213698
0.767	Intermediate Similarity	NPC52044
0.767	Intermediate Similarity	NPC67584
0.767	Intermediate Similarity	NPC91408
0.767	Intermediate Similarity	NPC476174
0.767	Intermediate Similarity	NPC37408
0.767	Intermediate Similarity	NPC170120
0.767	Intermediate Similarity	NPC472932
0.7667	Intermediate Similarity	NPC477366
0.7667	Intermediate Similarity	NPC477363
0.7664	Intermediate Similarity	NPC472747
0.7664	Intermediate Similarity	NPC472750
0.7658	Intermediate Similarity	NPC260786
0.7658	Intermediate Similarity	NPC96739
0.7658	Intermediate Similarity	NPC174471
0.7658	Intermediate Similarity	NPC287311
0.7658	Intermediate Similarity	NPC474871
0.7652	Intermediate Similarity	NPC472933
0.7652	Intermediate Similarity	NPC5989
0.7652	Intermediate Similarity	NPC275696
0.7652	Intermediate Similarity	NPC22628
0.7652	Intermediate Similarity	NPC471108
0.7652	Intermediate Similarity	NPC255081
0.7652	Intermediate Similarity	NPC61520
0.7652	Intermediate Similarity	NPC5991
0.7647	Intermediate Similarity	NPC37816
0.7642	Intermediate Similarity	NPC99411
0.7642	Intermediate Similarity	NPC206079
0.7642	Intermediate Similarity	NPC476270
0.7642	Intermediate Similarity	NPC146822
0.7642	Intermediate Similarity	NPC81530
0.7642	Intermediate Similarity	NPC150923
0.7636	Intermediate Similarity	NPC214644
0.7636	Intermediate Similarity	NPC77089
0.7636	Intermediate Similarity	NPC477102
0.7632	Intermediate Similarity	NPC153651
0.7632	Intermediate Similarity	NPC156252
0.7632	Intermediate Similarity	NPC472934
0.7629	Intermediate Similarity	NPC108045
0.7629	Intermediate Similarity	NPC475622
0.7624	Intermediate Similarity	NPC477711
0.7624	Intermediate Similarity	NPC129419
0.7623	Intermediate Similarity	NPC37968
0.7619	Intermediate Similarity	NPC64742
0.7619	Intermediate Similarity	NPC235464
0.7619	Intermediate Similarity	NPC166745
0.7619	Intermediate Similarity	NPC10364
0.7611	Intermediate Similarity	NPC67290

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 NPC118405 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	2067
0.2-0.3	3833
0.3-0.4	2092
0.4-0.5	520
0.5-0.6	210
0.6-0.7	152
0.7-0.8	58
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
0.8037	Intermediate Similarity	NPD6899	Approved
0.8037	Intermediate Similarity	NPD6881	Approved
0.8019	Intermediate Similarity	NPD7128	Approved
0.8019	Intermediate Similarity	NPD5739	Approved
0.8019	Intermediate Similarity	NPD6675	Approved
0.8019	Intermediate Similarity	NPD6402	Approved
0.7982	Intermediate Similarity	NPD6649	Approved
0.7982	Intermediate Similarity	NPD6650	Approved
0.798	Intermediate Similarity	NPD5785	Approved
0.7963	Intermediate Similarity	NPD6373	Approved
0.7963	Intermediate Similarity	NPD6372	Approved
0.7944	Intermediate Similarity	NPD5697	Approved
0.7895	Intermediate Similarity	NPD6435	Approved
0.789	Intermediate Similarity	NPD7102	Approved
0.789	Intermediate Similarity	NPD6371	Approved
0.789	Intermediate Similarity	NPD7290	Approved
0.789	Intermediate Similarity	NPD6883	Approved
0.787	Intermediate Similarity	NPD7320	Approved
0.7864	Intermediate Similarity	NPD6084	Phase 2
0.7864	Intermediate Similarity	NPD6083	Phase 2
0.7835	Intermediate Similarity	NPD5363	Approved
0.7818	Intermediate Similarity	NPD8130	Phase 1
0.7818	Intermediate Similarity	NPD6869	Approved
0.7818	Intermediate Similarity	NPD6617	Approved
0.7818	Intermediate Similarity	NPD6847	Approved
0.7798	Intermediate Similarity	NPD6013	Approved
0.7798	Intermediate Similarity	NPD6012	Approved
0.7798	Intermediate Similarity	NPD6014	Approved
0.7778	Intermediate Similarity	NPD5701	Approved
0.7755	Intermediate Similarity	NPD5786	Approved
0.7748	Intermediate Similarity	NPD6882	Approved
0.7748	Intermediate Similarity	NPD8297	Approved
0.7706	Intermediate Similarity	NPD6011	Approved
0.7684	Intermediate Similarity	NPD4821	Approved
0.7684	Intermediate Similarity	NPD4822	Approved
0.7684	Intermediate Similarity	NPD4819	Approved
0.7684	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5368	Approved
0.7684	Intermediate Similarity	NPD4820	Approved
0.767	Intermediate Similarity	NPD5695	Phase 3
0.7629	Intermediate Similarity	NPD5362	Discontinued
0.7619	Intermediate Similarity	NPD5696	Approved
0.757	Intermediate Similarity	NPD5211	Phase 2
0.7526	Intermediate Similarity	NPD4270	Approved
0.7526	Intermediate Similarity	NPD4269	Approved
0.75	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD4268	Approved
0.7474	Intermediate Similarity	NPD4271	Approved
0.7449	Intermediate Similarity	NPD7154	Phase 3
0.7431	Intermediate Similarity	NPD5141	Approved
0.7423	Intermediate Similarity	NPD5369	Approved
0.7391	Intermediate Similarity	NPD6274	Approved
0.7383	Intermediate Similarity	NPD5286	Approved
0.7383	Intermediate Similarity	NPD5285	Approved
0.7383	Intermediate Similarity	NPD4696	Approved
0.7358	Intermediate Similarity	NPD4755	Approved
0.735	Intermediate Similarity	NPD7100	Approved
0.735	Intermediate Similarity	NPD7101	Approved
0.732	Intermediate Similarity	NPD4252	Approved
0.7297	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6053	Discontinued
0.7265	Intermediate Similarity	NPD6335	Approved
0.725	Intermediate Similarity	NPD7604	Phase 2
0.7248	Intermediate Similarity	NPD5224	Approved
0.7248	Intermediate Similarity	NPD5225	Approved
0.7248	Intermediate Similarity	NPD4633	Approved
0.7248	Intermediate Similarity	NPD5226	Approved
0.7222	Intermediate Similarity	NPD4700	Approved
0.7184	Intermediate Similarity	NPD4753	Phase 2
0.7184	Intermediate Similarity	NPD6080	Approved
0.7184	Intermediate Similarity	NPD6673	Approved
0.7184	Intermediate Similarity	NPD6904	Approved
0.7182	Intermediate Similarity	NPD5174	Approved
0.7182	Intermediate Similarity	NPD5175	Approved
0.7179	Intermediate Similarity	NPD7115	Discovery
0.7179	Intermediate Similarity	NPD6317	Approved
0.717	Intermediate Similarity	NPD4629	Approved
0.717	Intermediate Similarity	NPD5210	Approved
0.7157	Intermediate Similarity	NPD4250	Approved
0.7157	Intermediate Similarity	NPD4251	Approved
0.7156	Intermediate Similarity	NPD5223	Approved
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD6319	Approved
0.7129	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6314	Approved
0.7119	Intermediate Similarity	NPD6313	Approved
0.71	Intermediate Similarity	NPD5331	Approved
0.71	Intermediate Similarity	NPD5332	Approved
0.7087	Intermediate Similarity	NPD5737	Approved
0.7087	Intermediate Similarity	NPD6672	Approved
0.7083	Intermediate Similarity	NPD6909	Approved
0.7083	Intermediate Similarity	NPD6908	Approved
0.7071	Intermediate Similarity	NPD4790	Discontinued
0.7069	Intermediate Similarity	NPD4632	Approved
0.7059	Intermediate Similarity	NPD4249	Approved
0.7054	Intermediate Similarity	NPD6008	Approved
0.7049	Intermediate Similarity	NPD7492	Approved
0.7048	Intermediate Similarity	NPD5693	Phase 1
0.7048	Intermediate Similarity	NPD6050	Approved
0.7034	Intermediate Similarity	NPD6009	Approved
0.7009	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6054	Approved
0.6992	Remote Similarity	NPD6616	Approved
0.6952	Remote Similarity	NPD5692	Phase 3
0.6942	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5983	Phase 2
0.6935	Remote Similarity	NPD7078	Approved
0.693	Remote Similarity	NPD4729	Approved
0.693	Remote Similarity	NPD5128	Approved
0.693	Remote Similarity	NPD4730	Approved
0.6916	Remote Similarity	NPD5282	Discontinued
0.6903	Remote Similarity	NPD4767	Approved
0.6903	Remote Similarity	NPD4768	Approved
0.6893	Remote Similarity	NPD7334	Approved
0.6893	Remote Similarity	NPD7146	Approved
0.6893	Remote Similarity	NPD5330	Approved
0.6893	Remote Similarity	NPD6684	Approved
0.6893	Remote Similarity	NPD6409	Approved
0.6893	Remote Similarity	NPD7521	Approved
0.6893	Remote Similarity	NPD6098	Approved
0.6887	Remote Similarity	NPD5281	Approved
0.6887	Remote Similarity	NPD5694	Approved
0.6887	Remote Similarity	NPD5284	Approved
0.6885	Remote Similarity	NPD6370	Approved
0.688	Remote Similarity	NPD7736	Approved
0.6875	Remote Similarity	NPD4754	Approved
0.686	Remote Similarity	NPD6059	Approved
0.6857	Remote Similarity	NPD1695	Approved
0.6855	Remote Similarity	NPD6336	Discontinued
0.6822	Remote Similarity	NPD5779	Approved
0.6822	Remote Similarity	NPD5778	Approved
0.681	Remote Similarity	NPD5250	Approved
0.681	Remote Similarity	NPD4634	Approved
0.681	Remote Similarity	NPD5251	Approved
0.681	Remote Similarity	NPD5248	Approved
0.681	Remote Similarity	NPD5249	Phase 3
0.681	Remote Similarity	NPD5247	Approved
0.6807	Remote Similarity	NPD6868	Approved
0.6803	Remote Similarity	NPD6016	Approved
0.6803	Remote Similarity	NPD6015	Approved
0.68	Remote Similarity	NPD8293	Discontinued
0.6796	Remote Similarity	NPD5329	Approved
0.6792	Remote Similarity	NPD6698	Approved
0.6792	Remote Similarity	NPD46	Approved
0.6789	Remote Similarity	NPD5222	Approved
0.6789	Remote Similarity	NPD4697	Phase 3
0.6789	Remote Similarity	NPD5221	Approved
0.6789	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6903	Approved
0.6762	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7640	Approved
0.6757	Remote Similarity	NPD7639	Approved
0.6752	Remote Similarity	NPD5217	Approved
0.6752	Remote Similarity	NPD5216	Approved
0.6752	Remote Similarity	NPD5215	Approved
0.6748	Remote Similarity	NPD5988	Approved
0.6731	Remote Similarity	NPD5690	Phase 2
0.6731	Remote Similarity	NPD5279	Phase 3
0.6729	Remote Similarity	NPD7983	Approved
0.6729	Remote Similarity	NPD6079	Approved
0.6729	Remote Similarity	NPD7637	Suspended
0.6729	Remote Similarity	NPD6411	Approved
0.6727	Remote Similarity	NPD5959	Approved
0.6727	Remote Similarity	NPD5173	Approved
0.6699	Remote Similarity	NPD4197	Approved
0.6699	Remote Similarity	NPD3665	Phase 1
0.6699	Remote Similarity	NPD3133	Approved
0.6699	Remote Similarity	NPD3666	Approved
0.6698	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD1696	Phase 3
0.661	Remote Similarity	NPD5127	Approved
0.6606	Remote Similarity	NPD6001	Approved
0.6587	Remote Similarity	NPD7507	Approved
0.6571	Remote Similarity	NPD5280	Approved
0.6571	Remote Similarity	NPD4694	Approved
0.6552	Remote Similarity	NPD6412	Phase 2
0.6552	Remote Similarity	NPD6614	Approved
0.6545	Remote Similarity	NPD5654	Approved
0.6542	Remote Similarity	NPD6101	Approved
0.6542	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4786	Approved
0.6538	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4223	Phase 3
0.6505	Remote Similarity	NPD4221	Approved
0.6505	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4756	Discovery
0.6496	Remote Similarity	NPD6686	Approved
0.6481	Remote Similarity	NPD5207	Approved
0.6481	Remote Similarity	NPD7838	Discovery
0.6476	Remote Similarity	NPD1733	Clinical (unspecified phase)

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