NPASS Compound

Structure

NPC472399 OpenBabel07101718202D 39 42 0 0 1 0 0 0 0 0999 V2000 2.5305 4.5384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7917 3.9736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8136 3.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 2.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2521 -1.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5903 0.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 -0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 -1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5454 3.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7767 2.9738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4921 -0.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4412 -3.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0938 -4.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6870 3.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9033 2.4868 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3011 -1.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4452 -3.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8884 -1.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7541 -2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 -0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9921 -2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7019 2.0257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8884 1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8584 -0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 -2.2764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7468 -0.9740 0.0000 C 0 0 2 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 0.1073 -4.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1969 -2.7868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5799 -3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5753 1.5387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2232 -2.9158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3265 -1.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8435 1.5128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 27 1 0 0 0 0 8 27 1 0 0 0 0 9 14 2 0 0 0 0 10 15 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 18 2 0 0 0 0 12 28 1 0 0 0 0 13 18 1 0 0 0 0 13 31 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 17 29 1 1 0 0 0 18 21 1 0 0 0 0 19 28 1 6 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 29 1 1 0 0 0 21 32 2 0 0 0 0 22 27 1 0 0 0 0 22 30 1 1 0 0 0 23 28 1 0 0 0 0 23 33 2 0 0 0 0 24 30 1 6 0 0 0 24 38 1 0 0 0 0 25 34 2 0 0 0 0 25 38 1 0 0 0 0 26 35 2 0 0 0 0 26 39 1 0 0 0 0 27 30 1 0 0 0 0 28 36 1 6 0 0 0 29 37 1 1 0 0 0 30 39 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	544.27
Volume:	553.867
LogP:	3.149
LogD:	1.638
LogS:	-4.102
# Rotatable Bonds:	8
TPSA:	147.43
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	5.581
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
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:	-5.005
MDCK Permeability:	1.1747677490347996e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.084
20% Bioavailability (F20%):	0.323
30% Bioavailability (F30%):	0.862

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.548
Plasma Protein Binding (PPB):	73.11846160888672%
Volume Distribution (VD):	1.273
Pgp-substrate:	22.478927612304688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.388
CYP2C19-substrate:	0.662
CYP2C9-inhibitor:	0.476
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.791
CYP3A4-substrate:	0.534

ADMET: Excretion

Clearance (CL):	3.496
Half-life (T1/2):	0.188

ADMET: Toxicity

hERG Blockers:	0.59
Human Hepatotoxicity (H-HT):	0.969
Drug-inuced Liver Injury (DILI):	0.168
AMES Toxicity:	0.162
Rat Oral Acute Toxicity:	0.324
Maximum Recommended Daily Dose:	0.447
Skin Sensitization:	0.552
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.011
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: NPC472399

Natural Product ID:	NPC472399
*Common Name:**	WXDWVELLVNXGSM-MIDVLLHRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WXDWVELLVNXGSM-MIDVLLHRSA-N
Standard InCHI:	InChI=1S/C30H40O9/c1-9-14(3)25(34)38-24-17(6)29(37)19-11-16(5)23(33)28(19,36)12-18(13-31)21(32)20(29)22-27(7,8)30(22,24)39-26(35)15(4)10-2/h9,11-12,15,17,19-20,22,24,31,36-37H,10,13H2,1-8H3/b14-9+/t15?,17-,19-,20+,22-,24-,28-,29+,30-/m1/s1
SMILES:	CCC(C)C(=O)OC12C(C1(C)C)C3C(=O)C(=CC4(C(C3(C(C2OC(=O)C(=CC)C)C)O)C=C(C4=O)C)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3400660
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

*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
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049973]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23701597]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25819096]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2978	Croton tiglium	Species	Euphorbiaceae	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	14

Activity Type	# Activity
Cell Line	8
Individual Protein	2
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	17000.0	nM	PMID[555738]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	4800.0	nM	PMID[555738]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	20000.0	nM	PMID[555738]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	5000.0	nM	PMID[555738]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	10000.0	nM	PMID[555738]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	19000.0	nM	PMID[555738]
NPT2341	Cell Line	NCI-H1975	Homo sapiens	IC50	=	10000.0	nM	PMID[555738]
NPT2615	Cell Line	HEK-293T	Homo sapiens	IC50	=	455300.0	nM	PMID[555738]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	>	50000.0	nM	PMID[555738]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	50000.0	nM	PMID[555738]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21000.0	nM	PMID[555738]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	23000.0	nM	PMID[555738]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10000.0	nM	PMID[555738]
NPT27	Others	Unspecified		IC50	>	500000.0	nM	PMID[555738]

☑ 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 NPC472399 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	263
0.1-0.2	1567
0.2-0.3	4402
0.3-0.4	6926
0.4-0.5	12779
0.5-0.6	9319
0.6-0.7	5643
0.7-0.8	1522
0.8-0.85	149
0.85-0.9	37
0.9-0.95	72
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9823	High Similarity	NPC472401
0.9737	High Similarity	NPC19464
0.9735	High Similarity	NPC145182
0.9735	High Similarity	NPC157252
0.9735	High Similarity	NPC471126
0.9735	High Similarity	NPC471128
0.9649	High Similarity	NPC52839
0.9558	High Similarity	NPC472397
0.9558	High Similarity	NPC471125
0.9558	High Similarity	NPC171905
0.9558	High Similarity	NPC472758
0.9474	High Similarity	NPC22628
0.9474	High Similarity	NPC5991
0.9474	High Similarity	NPC275696
0.9474	High Similarity	NPC471108
0.9474	High Similarity	NPC255081
0.9474	High Similarity	NPC5989
0.9402	High Similarity	NPC145238
0.9397	High Similarity	NPC257017
0.9397	High Similarity	NPC162009
0.9381	High Similarity	NPC471127
0.9381	High Similarity	NPC154363
0.9381	High Similarity	NPC234858
0.9298	High Similarity	NPC156252
0.9298	High Similarity	NPC10721
0.9292	High Similarity	NPC474872
0.9237	High Similarity	NPC473709
0.9237	High Similarity	NPC473919
0.9204	High Similarity	NPC71889
0.9204	High Similarity	NPC472757
0.9153	High Similarity	NPC473802
0.9138	High Similarity	NPC156745
0.9138	High Similarity	NPC236918
0.9123	High Similarity	NPC472400
0.9115	High Similarity	NPC475391
0.9083	High Similarity	NPC471940
0.906	High Similarity	NPC329080
0.906	High Similarity	NPC19336
0.906	High Similarity	NPC475885
0.906	High Similarity	NPC472759
0.906	High Similarity	NPC185876
0.9052	High Similarity	NPC124676
0.9052	High Similarity	NPC146280
0.9035	High Similarity	NPC474937
0.9027	High Similarity	NPC158523
0.9027	High Similarity	NPC174471
0.9027	High Similarity	NPC474871
0.9027	High Similarity	NPC475937
0.9027	High Similarity	NPC96739
0.9027	High Similarity	NPC260786
0.9008	High Similarity	NPC236999
0.9008	High Similarity	NPC270109
0.9	High Similarity	NPC471939
0.8974	High Similarity	NPC180640
0.8947	High Similarity	NPC89227
0.8947	High Similarity	NPC101825
0.8947	High Similarity	NPC151216
0.8947	High Similarity	NPC17138
0.8947	High Similarity	NPC221511
0.8947	High Similarity	NPC215643
0.8947	High Similarity	NPC170212
0.8947	High Similarity	NPC265499
0.8938	High Similarity	NPC153036
0.8889	High Similarity	NPC472760
0.8843	High Similarity	NPC222307
0.8803	High Similarity	NPC153651
0.8684	High Similarity	NPC163004
0.8655	High Similarity	NPC472667
0.864	High Similarity	NPC475139
0.864	High Similarity	NPC180902
0.8547	High Similarity	NPC477091
0.8537	High Similarity	NPC217901
0.8522	High Similarity	NPC273433
0.8504	High Similarity	NPC182266
0.8504	High Similarity	NPC471137
0.8504	High Similarity	NPC223356
0.8504	High Similarity	NPC471136
0.8504	High Similarity	NPC475500
0.8504	High Similarity	NPC475154
0.8504	High Similarity	NPC100017
0.8504	High Similarity	NPC473548
0.848	Intermediate Similarity	NPC162495
0.8468	Intermediate Similarity	NPC168849
0.8468	Intermediate Similarity	NPC475273
0.843	Intermediate Similarity	NPC143755
0.843	Intermediate Similarity	NPC472004
0.8417	Intermediate Similarity	NPC251310
0.8413	Intermediate Similarity	NPC251564
0.8413	Intermediate Similarity	NPC475606
0.8413	Intermediate Similarity	NPC475314
0.8413	Intermediate Similarity	NPC477189
0.839	Intermediate Similarity	NPC477126
0.8387	Intermediate Similarity	NPC293112
0.8374	Intermediate Similarity	NPC67251
0.8372	Intermediate Similarity	NPC243902
0.8372	Intermediate Similarity	NPC68282
0.8361	Intermediate Similarity	NPC310511
0.8359	Intermediate Similarity	NPC476823
0.8348	Intermediate Similarity	NPC474716
0.8346	Intermediate Similarity	NPC474508
0.8346	Intermediate Similarity	NPC473485
0.8333	Intermediate Similarity	NPC469684
0.8333	Intermediate Similarity	NPC231529
0.8306	Intermediate Similarity	NPC470922
0.8306	Intermediate Similarity	NPC81736
0.8306	Intermediate Similarity	NPC476729
0.8306	Intermediate Similarity	NPC24651
0.8306	Intermediate Similarity	NPC172154
0.8305	Intermediate Similarity	NPC317687
0.8293	Intermediate Similarity	NPC222688
0.8293	Intermediate Similarity	NPC269642
0.8291	Intermediate Similarity	NPC477103
0.8291	Intermediate Similarity	NPC257240
0.8281	Intermediate Similarity	NPC476111
0.8281	Intermediate Similarity	NPC469673
0.8268	Intermediate Similarity	NPC196921
0.8268	Intermediate Similarity	NPC476855
0.8268	Intermediate Similarity	NPC220757
0.8254	Intermediate Similarity	NPC476859
0.825	Intermediate Similarity	NPC476710
0.825	Intermediate Similarity	NPC179626
0.825	Intermediate Similarity	NPC476711
0.824	Intermediate Similarity	NPC473635
0.8226	Intermediate Similarity	NPC469789
0.8226	Intermediate Similarity	NPC11895
0.8226	Intermediate Similarity	NPC105926
0.8226	Intermediate Similarity	NPC265557
0.8226	Intermediate Similarity	NPC91693
0.8226	Intermediate Similarity	NPC18945
0.822	Intermediate Similarity	NPC287311
0.822	Intermediate Similarity	NPC317107
0.8211	Intermediate Similarity	NPC470779
0.8211	Intermediate Similarity	NPC4021
0.8211	Intermediate Similarity	NPC159456
0.8205	Intermediate Similarity	NPC42662
0.8205	Intermediate Similarity	NPC477102
0.8203	Intermediate Similarity	NPC34963
0.8197	Intermediate Similarity	NPC470186
0.8189	Intermediate Similarity	NPC35109
0.8189	Intermediate Similarity	NPC476854
0.8189	Intermediate Similarity	NPC470851
0.8182	Intermediate Similarity	NPC476712
0.8182	Intermediate Similarity	NPC476713
0.8182	Intermediate Similarity	NPC474654
0.8182	Intermediate Similarity	NPC470854
0.8182	Intermediate Similarity	NPC296822
0.8182	Intermediate Similarity	NPC470775
0.8182	Intermediate Similarity	NPC97908
0.8182	Intermediate Similarity	NPC122033
0.8182	Intermediate Similarity	NPC287343
0.8182	Intermediate Similarity	NPC176513
0.8175	Intermediate Similarity	NPC470882
0.8151	Intermediate Similarity	NPC471933
0.8151	Intermediate Similarity	NPC473877
0.8151	Intermediate Similarity	NPC269530
0.8145	Intermediate Similarity	NPC23786
0.8145	Intermediate Similarity	NPC312833
0.8145	Intermediate Similarity	NPC470265
0.8145	Intermediate Similarity	NPC170538
0.814	Intermediate Similarity	NPC58029
0.814	Intermediate Similarity	NPC469674
0.8136	Intermediate Similarity	NPC5103
0.813	Intermediate Similarity	NPC154491
0.813	Intermediate Similarity	NPC268530
0.813	Intermediate Similarity	NPC251226
0.813	Intermediate Similarity	NPC4548
0.813	Intermediate Similarity	NPC475003
0.813	Intermediate Similarity	NPC112038
0.8125	Intermediate Similarity	NPC279478
0.8125	Intermediate Similarity	NPC476862
0.8125	Intermediate Similarity	NPC241935
0.8125	Intermediate Similarity	NPC476852
0.8125	Intermediate Similarity	NPC476863
0.8125	Intermediate Similarity	NPC473838
0.8125	Intermediate Similarity	NPC475389
0.812	Intermediate Similarity	NPC29827
0.812	Intermediate Similarity	NPC322903
0.812	Intermediate Similarity	NPC476479
0.8115	Intermediate Similarity	NPC240509
0.811	Intermediate Similarity	NPC470850
0.8103	Intermediate Similarity	NPC103088
0.8103	Intermediate Similarity	NPC470975
0.8103	Intermediate Similarity	NPC470979
0.8099	Intermediate Similarity	NPC474333
0.8099	Intermediate Similarity	NPC477509
0.8099	Intermediate Similarity	NPC270478
0.8099	Intermediate Similarity	NPC470793
0.8095	Intermediate Similarity	NPC225049
0.8083	Intermediate Similarity	NPC7921
0.8083	Intermediate Similarity	NPC469454
0.8083	Intermediate Similarity	NPC469463
0.8083	Intermediate Similarity	NPC46269
0.8083	Intermediate Similarity	NPC469496
0.8083	Intermediate Similarity	NPC470120
0.8083	Intermediate Similarity	NPC208998
0.8083	Intermediate Similarity	NPC106395
0.808	Intermediate Similarity	NPC469352
0.8067	Intermediate Similarity	NPC474846
0.8067	Intermediate Similarity	NPC469656
0.8067	Intermediate Similarity	NPC469655

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 NPC472399 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	1968
0.2-0.3	3568
0.3-0.4	2129
0.4-0.5	799
0.5-0.6	286
0.6-0.7	152
0.7-0.8	13
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
0.8291	Intermediate Similarity	NPD6371	Approved
0.7815	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7115	Discovery
0.7698	Intermediate Similarity	NPD6319	Approved
0.7583	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD8297	Approved
0.7541	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7319	Approved
0.748	Intermediate Similarity	NPD6649	Approved
0.748	Intermediate Similarity	NPD6650	Approved
0.7462	Intermediate Similarity	NPD7492	Approved
0.7459	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6372	Approved
0.7459	Intermediate Similarity	NPD6373	Approved
0.7458	Intermediate Similarity	NPD5344	Discontinued
0.7436	Intermediate Similarity	NPD4225	Approved
0.7422	Intermediate Similarity	NPD6054	Approved
0.7405	Intermediate Similarity	NPD6616	Approved
0.7385	Intermediate Similarity	NPD7604	Phase 2
0.7377	Intermediate Similarity	NPD6899	Approved
0.7377	Intermediate Similarity	NPD6881	Approved
0.736	Intermediate Similarity	NPD4632	Approved
0.7355	Intermediate Similarity	NPD6675	Approved
0.7355	Intermediate Similarity	NPD6402	Approved
0.7355	Intermediate Similarity	NPD7128	Approved
0.7355	Intermediate Similarity	NPD5739	Approved
0.7348	Intermediate Similarity	NPD7078	Approved
0.7308	Intermediate Similarity	NPD6370	Approved
0.7295	Intermediate Similarity	NPD5697	Approved
0.7295	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7736	Approved
0.7287	Intermediate Similarity	NPD6059	Approved
0.728	Intermediate Similarity	NPD6882	Approved
0.7273	Intermediate Similarity	NPD7507	Approved
0.7258	Intermediate Similarity	NPD6883	Approved
0.7258	Intermediate Similarity	NPD7102	Approved
0.7258	Intermediate Similarity	NPD7290	Approved
0.7236	Intermediate Similarity	NPD7320	Approved
0.7231	Intermediate Similarity	NPD6921	Approved
0.7231	Intermediate Similarity	NPD6016	Approved
0.7231	Intermediate Similarity	NPD6015	Approved
0.7227	Intermediate Similarity	NPD6648	Approved
0.7227	Intermediate Similarity	NPD7640	Approved
0.7227	Intermediate Similarity	NPD7639	Approved
0.7218	Intermediate Similarity	NPD8293	Discontinued
0.72	Intermediate Similarity	NPD6847	Approved
0.72	Intermediate Similarity	NPD8130	Phase 1
0.72	Intermediate Similarity	NPD6617	Approved
0.72	Intermediate Similarity	NPD6869	Approved
0.7188	Intermediate Similarity	NPD6009	Approved
0.7179	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6013	Approved
0.7177	Intermediate Similarity	NPD6014	Approved
0.7177	Intermediate Similarity	NPD6012	Approved
0.7176	Intermediate Similarity	NPD5988	Approved
0.7154	Intermediate Similarity	NPD5701	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.7121	Intermediate Similarity	NPD8328	Phase 3
0.712	Intermediate Similarity	NPD4634	Approved
0.7107	Intermediate Similarity	NPD5211	Phase 2
0.7099	Intermediate Similarity	NPD5983	Phase 2
0.7097	Intermediate Similarity	NPD6686	Approved
0.7097	Intermediate Similarity	NPD6011	Approved
0.7077	Intermediate Similarity	NPD7516	Approved
0.7073	Intermediate Similarity	NPD6008	Approved
0.7015	Intermediate Similarity	NPD6336	Discontinued
0.7008	Intermediate Similarity	NPD6053	Discontinued
0.7	Intermediate Similarity	NPD7327	Approved
0.7	Intermediate Similarity	NPD7328	Approved
0.6992	Remote Similarity	NPD5141	Approved
0.6983	Remote Similarity	NPD6698	Approved
0.6983	Remote Similarity	NPD46	Approved
0.6942	Remote Similarity	NPD4696	Approved
0.6942	Remote Similarity	NPD5285	Approved
0.6942	Remote Similarity	NPD5286	Approved
0.6929	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4755	Approved
0.6846	Remote Similarity	NPD6274	Approved
0.6842	Remote Similarity	NPD8516	Approved
0.6842	Remote Similarity	NPD8513	Phase 3
0.6842	Remote Similarity	NPD8515	Approved
0.6842	Remote Similarity	NPD8517	Approved
0.6838	Remote Similarity	NPD5785	Approved
0.6829	Remote Similarity	NPD5225	Approved
0.6829	Remote Similarity	NPD5224	Approved
0.6829	Remote Similarity	NPD5226	Approved
0.6829	Remote Similarity	NPD4633	Approved
0.6818	Remote Similarity	NPD7101	Approved
0.6818	Remote Similarity	NPD7100	Approved
0.6807	Remote Similarity	NPD5282	Discontinued
0.6803	Remote Similarity	NPD4700	Approved
0.6794	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6033	Approved
0.678	Remote Similarity	NPD7983	Approved
0.6777	Remote Similarity	NPD6084	Phase 2
0.6777	Remote Similarity	NPD6083	Phase 2
0.6774	Remote Similarity	NPD5175	Approved
0.6774	Remote Similarity	NPD5174	Approved
0.6763	Remote Similarity	NPD7260	Phase 2
0.6748	Remote Similarity	NPD5223	Approved
0.6748	Remote Similarity	NPD1700	Approved
0.6742	Remote Similarity	NPD6335	Approved
0.6723	Remote Similarity	NPD5778	Approved
0.6723	Remote Similarity	NPD5779	Approved
0.6716	Remote Similarity	NPD8380	Approved
0.6716	Remote Similarity	NPD8335	Approved
0.6716	Remote Similarity	NPD8033	Approved
0.6716	Remote Similarity	NPD8378	Approved
0.6716	Remote Similarity	NPD8379	Approved
0.6716	Remote Similarity	NPD8296	Approved
0.6694	Remote Similarity	NPD7632	Discontinued
0.6693	Remote Similarity	NPD4730	Approved
0.6693	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6642	Remote Similarity	NPD8377	Approved
0.6642	Remote Similarity	NPD8294	Approved
0.6617	Remote Similarity	NPD6314	Approved
0.6617	Remote Similarity	NPD6313	Approved
0.6612	Remote Similarity	NPD5695	Phase 3
0.661	Remote Similarity	NPD1695	Approved
0.6594	Remote Similarity	NPD8074	Phase 3
0.6593	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6908	Approved
0.6593	Remote Similarity	NPD6909	Approved
0.6593	Remote Similarity	NPD7503	Approved
0.6589	Remote Similarity	NPD5248	Approved
0.6589	Remote Similarity	NPD5249	Phase 3
0.6589	Remote Similarity	NPD5250	Approved
0.6589	Remote Similarity	NPD5251	Approved
0.6589	Remote Similarity	NPD5247	Approved
0.6585	Remote Similarity	NPD5696	Approved
0.6583	Remote Similarity	NPD6399	Phase 3
0.6565	Remote Similarity	NPD8133	Approved
0.6562	Remote Similarity	NPD5128	Approved
0.6557	Remote Similarity	NPD5222	Approved
0.6557	Remote Similarity	NPD4697	Phase 3
0.6557	Remote Similarity	NPD5221	Approved
0.6557	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7838	Discovery
0.6552	Remote Similarity	NPD1696	Phase 3
0.6538	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD4754	Approved
0.6504	Remote Similarity	NPD7902	Approved
0.6504	Remote Similarity	NPD5173	Approved
0.65	Remote Similarity	NPD7637	Suspended
0.65	Remote Similarity	NPD6079	Approved
0.6484	Remote Similarity	NPD6412	Phase 2
0.6479	Remote Similarity	NPD6845	Suspended
0.6475	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5328	Approved
0.6466	Remote Similarity	NPD6868	Approved
0.6452	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD5216	Approved
0.6412	Remote Similarity	NPD5217	Approved
0.6412	Remote Similarity	NPD5215	Approved
0.641	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5363	Approved
0.641	Remote Similarity	NPD1694	Approved
0.6393	Remote Similarity	NPD7748	Approved
0.6364	Remote Similarity	NPD7515	Phase 2
0.6364	Remote Similarity	NPD5693	Phase 1
0.6364	Remote Similarity	NPD6411	Approved
0.6356	Remote Similarity	NPD5786	Approved
0.6341	Remote Similarity	NPD4629	Approved
0.6341	Remote Similarity	NPD5210	Approved
0.6336	Remote Similarity	NPD5135	Approved
0.6336	Remote Similarity	NPD5169	Approved
0.6336	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4753	Phase 2
0.6311	Remote Similarity	NPD4202	Approved
0.6301	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD5127	Approved
0.626	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7900	Approved
0.6259	Remote Similarity	NPD6333	Approved
0.6259	Remote Similarity	NPD6334	Approved
0.6259	Remote Similarity	NPD7642	Approved
0.625	Remote Similarity	NPD5737	Approved
0.625	Remote Similarity	NPD6672	Approved
0.6224	Remote Similarity	NPD5956	Approved
0.6218	Remote Similarity	NPD3618	Phase 1
0.6198	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6673	Approved
0.6198	Remote Similarity	NPD6080	Approved
0.6198	Remote Similarity	NPD6101	Approved
0.6198	Remote Similarity	NPD6904	Approved
0.6169	Remote Similarity	NPD7236	Approved
0.6168	Remote Similarity	NPD7799	Discontinued
0.6167	Remote Similarity	NPD7524	Approved
0.6167	Remote Similarity	NPD3573	Approved
0.6163	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.616	Remote Similarity	NPD7839	Suspended
0.6154	Remote Similarity	NPD4270	Approved
0.6154	Remote Similarity	NPD5209	Approved
0.6154	Remote Similarity	NPD4269	Approved
0.6148	Remote Similarity	NPD5167	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