NPASS Compound

Structure

NPC471939 OpenBabel07101718282D 43 46 0 0 1 0 0 0 0 0999 V2000 -0.3115 -6.8055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4890 5.0596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9442 4.1901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6768 2.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0716 3.8919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8135 -5.9653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7921 -5.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2941 -5.1398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8174 -4.2849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3194 -3.4448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8428 -2.5899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3448 -1.7497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8682 -0.8949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3701 -0.0547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3488 -0.0694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8507 0.7708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3741 1.6256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9541 2.6427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3766 3.8665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6917 -0.4075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9656 4.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7459 2.0674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2314 3.3899 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1623 2.0674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3955 1.6403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4058 1.9093 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4435 1.1366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4490 2.3859 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2745 0.9395 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9256 0.3198 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4636 3.3646 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9508 0.2320 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2460 2.4113 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4648 1.1366 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5083 -1.3689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8935 0.8001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0188 0.3448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2892 1.8840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4276 -0.5204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8346 1.5233 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7122 0.5108 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4422 3.3499 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 6 1 0 0 0 0 2 21 2 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 7 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 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 25 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 19 31 1 0 0 0 0 20 35 1 0 0 0 0 22 27 1 0 0 0 0 23 33 1 1 0 0 0 24 33 1 6 0 0 0 24 34 1 0 0 0 0 25 36 2 0 0 0 0 25 42 1 0 0 0 0 26 28 1 0 0 0 0 26 29 1 0 0 0 0 26 33 1 1 0 0 0 27 34 1 0 0 0 0 27 37 2 0 0 0 0 28 31 1 1 0 0 0 28 38 1 0 0 0 0 29 32 1 1 0 0 0 29 43 1 0 0 0 0 30 32 1 6 0 0 0 30 34 1 0 0 0 0 30 39 1 0 0 0 0 31 21 1 6 0 0 0 31 42 1 0 0 0 0 32 20 1 6 0 0 0 32 43 1 0 0 0 0 33 40 1 1 0 0 0 34 41 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	602.35
Volume:	625.687
LogP:	4.73
LogD:	3.106
LogS:	-4.106
# Rotatable Bonds:	14
TPSA:	157.05
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.053
Synthetic Accessibility Score:	5.752
Fsp3:	0.706
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:	-4.966
MDCK Permeability:	2.8287113309488632e-05
Pgp-inhibitor:	0.37
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.751
20% Bioavailability (F20%):	0.942
30% Bioavailability (F30%):	0.682

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.228
Plasma Protein Binding (PPB):	97.57768249511719%
Volume Distribution (VD):	1.737
Pgp-substrate:	2.846108913421631%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.153
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.625
CYP2C9-inhibitor:	0.221
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.034
CYP3A4-inhibitor:	0.91
CYP3A4-substrate:	0.203

ADMET: Excretion

Clearance (CL):	2.663
Half-life (T1/2):	0.309

ADMET: Toxicity

hERG Blockers:	0.241
Human Hepatotoxicity (H-HT):	0.924
Drug-inuced Liver Injury (DILI):	0.702
AMES Toxicity:	0.41
Rat Oral Acute Toxicity:	0.981
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.506
Carcinogencity:	0.244
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC471939

Natural Product ID:	NPC471939
*Common Name:**	XJBXOYWCVGECEL-MBMZLHFWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XJBXOYWCVGECEL-MBMZLHFWSA-N
Standard InCHI:	InChI=1S/C34H50O9/c1-6-7-8-9-10-11-12-13-14-15-16-17-25(36)42-31(21(2)3)19-23(5)33(40)24-18-22(4)27(37)34(24,41)30(39)32(20-35)29(43-32)26(33)28(31)38/h14-18,23-24,26,28-30,35,38-41H,2,6-13,19-20H2,1,3-5H3/b15-14+,17-16-/t23-,24+,26-,28-,29+,30-,31-,32+,33+,34-/m1/s1
SMILES:	CCCCCCCCCC=CC=CC(=O)OC1(CC(C2(C3C=C(C(=O)C3(C(C4(C(C2C1O)O4)CO)O)O)C)O)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3309437
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:0003494] Rhamnofolane and daphnane 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
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[15997133]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[16141313]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	callus	n.a.	PMID[22368856]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23611151]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[24931277]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562066]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	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	1
Others	3

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2.7	nM	PMID[549661]
NPT81	Cell Line	A549	Homo sapiens	Activity	>	50.0	%	PMID[549661]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	17.57	%	PMID[549661]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	19.94	%	PMID[549661]

☑ 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 NPC471939 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	1455
0.2-0.3	4195
0.3-0.4	6908
0.4-0.5	12801
0.5-0.6	11183
0.6-0.7	4739
0.7-0.8	971
0.8-0.85	79
0.85-0.9	62
0.9-0.95	29
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9914	High Similarity	NPC471940
0.9826	High Similarity	NPC473802
0.9741	High Similarity	NPC473919
0.9741	High Similarity	NPC473709
0.9496	High Similarity	NPC236999
0.9426	High Similarity	NPC100017
0.9426	High Similarity	NPC182266
0.9426	High Similarity	NPC471137
0.9426	High Similarity	NPC471136
0.9426	High Similarity	NPC223356
0.9426	High Similarity	NPC473548
0.9426	High Similarity	NPC475154
0.9426	High Similarity	NPC475500
0.9274	High Similarity	NPC68282
0.9262	High Similarity	NPC473485
0.9262	High Similarity	NPC475139
0.9262	High Similarity	NPC180902
0.9262	High Similarity	NPC474508
0.918	High Similarity	NPC251564
0.918	High Similarity	NPC475606
0.918	High Similarity	NPC475314
0.918	High Similarity	NPC477189
0.9098	High Similarity	NPC162495
0.9083	High Similarity	NPC145238
0.9076	High Similarity	NPC162009
0.9076	High Similarity	NPC257017
0.9	High Similarity	NPC472399
0.8934	High Similarity	NPC168849
0.8934	High Similarity	NPC475273
0.8917	High Similarity	NPC19464
0.8852	High Similarity	NPC217901
0.8833	High Similarity	NPC472401
0.8833	High Similarity	NPC52839
0.875	High Similarity	NPC145182
0.875	High Similarity	NPC185876
0.875	High Similarity	NPC472759
0.875	High Similarity	NPC157252
0.875	High Similarity	NPC471126
0.875	High Similarity	NPC329080
0.875	High Similarity	NPC471128
0.875	High Similarity	NPC475885
0.875	High Similarity	NPC19336
0.8739	High Similarity	NPC124676
0.8739	High Similarity	NPC146280
0.872	High Similarity	NPC473838
0.872	High Similarity	NPC475389
0.8667	High Similarity	NPC470186
0.8667	High Similarity	NPC275696
0.8667	High Similarity	NPC180640
0.8667	High Similarity	NPC5991
0.8667	High Similarity	NPC236918
0.8667	High Similarity	NPC22628
0.8667	High Similarity	NPC156745
0.8667	High Similarity	NPC471108
0.8667	High Similarity	NPC255081
0.8667	High Similarity	NPC5989
0.8583	High Similarity	NPC472760
0.8583	High Similarity	NPC171905
0.8583	High Similarity	NPC471125
0.8583	High Similarity	NPC472397
0.8583	High Similarity	NPC472758
0.856	High Similarity	NPC476078
0.856	High Similarity	NPC476091
0.8512	High Similarity	NPC472667
0.85	High Similarity	NPC156252
0.85	High Similarity	NPC10721
0.85	High Similarity	NPC153651
0.8417	Intermediate Similarity	NPC154363
0.8417	Intermediate Similarity	NPC471127
0.8417	Intermediate Similarity	NPC234858
0.8413	Intermediate Similarity	NPC270109
0.8403	Intermediate Similarity	NPC474937
0.84	Intermediate Similarity	NPC473635
0.8362	Intermediate Similarity	NPC474716
0.8359	Intermediate Similarity	NPC470185
0.8333	Intermediate Similarity	NPC73314
0.8333	Intermediate Similarity	NPC472400
0.8333	Intermediate Similarity	NPC474872
0.8319	Intermediate Similarity	NPC471933
0.8319	Intermediate Similarity	NPC215643
0.8319	Intermediate Similarity	NPC17138
0.8319	Intermediate Similarity	NPC265499
0.8319	Intermediate Similarity	NPC221511
0.8319	Intermediate Similarity	NPC170212
0.8319	Intermediate Similarity	NPC89227
0.8319	Intermediate Similarity	NPC475391
0.8319	Intermediate Similarity	NPC151216
0.8319	Intermediate Similarity	NPC101825
0.8293	Intermediate Similarity	NPC143755
0.8293	Intermediate Similarity	NPC475003
0.8279	Intermediate Similarity	NPC284707
0.8264	Intermediate Similarity	NPC477509
0.8254	Intermediate Similarity	NPC293112
0.8254	Intermediate Similarity	NPC222307
0.825	Intermediate Similarity	NPC71889
0.825	Intermediate Similarity	NPC477126
0.825	Intermediate Similarity	NPC472757
0.824	Intermediate Similarity	NPC11895
0.824	Intermediate Similarity	NPC469352
0.8235	Intermediate Similarity	NPC174471
0.8235	Intermediate Similarity	NPC474871
0.8235	Intermediate Similarity	NPC260786
0.8235	Intermediate Similarity	NPC96739
0.8226	Intermediate Similarity	NPC310511
0.8203	Intermediate Similarity	NPC231529
0.8203	Intermediate Similarity	NPC475371
0.8197	Intermediate Similarity	NPC53396
0.8197	Intermediate Similarity	NPC98249
0.819	Intermediate Similarity	NPC474741
0.8175	Intermediate Similarity	NPC81736
0.8175	Intermediate Similarity	NPC172154
0.816	Intermediate Similarity	NPC170538
0.8145	Intermediate Similarity	NPC472004
0.8136	Intermediate Similarity	NPC29827
0.812	Intermediate Similarity	NPC470975
0.812	Intermediate Similarity	NPC103088
0.812	Intermediate Similarity	NPC470979
0.811	Intermediate Similarity	NPC470973
0.8103	Intermediate Similarity	NPC475945
0.8103	Intermediate Similarity	NPC475871
0.8099	Intermediate Similarity	NPC469496
0.8099	Intermediate Similarity	NPC469454
0.8099	Intermediate Similarity	NPC469463
0.8095	Intermediate Similarity	NPC469789
0.8083	Intermediate Similarity	NPC475937
0.8083	Intermediate Similarity	NPC158523
0.8067	Intermediate Similarity	NPC471934
0.8067	Intermediate Similarity	NPC273433
0.8065	Intermediate Similarity	NPC77689
0.8065	Intermediate Similarity	NPC473839
0.8065	Intermediate Similarity	NPC211093
0.8065	Intermediate Similarity	NPC473636
0.8062	Intermediate Similarity	NPC221414
0.8051	Intermediate Similarity	NPC266514
0.8051	Intermediate Similarity	NPC469558
0.8049	Intermediate Similarity	NPC474518
0.8049	Intermediate Similarity	NPC296822
0.8049	Intermediate Similarity	NPC476712
0.8049	Intermediate Similarity	NPC476713
0.8049	Intermediate Similarity	NPC469684
0.8033	Intermediate Similarity	NPC133677
0.8033	Intermediate Similarity	NPC138303
0.8033	Intermediate Similarity	NPC67290
0.8031	Intermediate Similarity	NPC24651
0.8017	Intermediate Similarity	NPC474747
0.8017	Intermediate Similarity	NPC317687
0.8017	Intermediate Similarity	NPC473877
0.8016	Intermediate Similarity	NPC23786
0.8016	Intermediate Similarity	NPC470265
0.8	Intermediate Similarity	NPC142882
0.8	Intermediate Similarity	NPC4548
0.8	Intermediate Similarity	NPC251226
0.8	Intermediate Similarity	NPC153036
0.7986	Intermediate Similarity	NPC251139
0.7984	Intermediate Similarity	NPC311554
0.7984	Intermediate Similarity	NPC257457
0.7984	Intermediate Similarity	NPC251310
0.7969	Intermediate Similarity	NPC181999
0.7969	Intermediate Similarity	NPC225049
0.7967	Intermediate Similarity	NPC470793
0.7967	Intermediate Similarity	NPC270478
0.7967	Intermediate Similarity	NPC474333
0.7967	Intermediate Similarity	NPC476710
0.7967	Intermediate Similarity	NPC476711
0.7955	Intermediate Similarity	NPC476823
0.7953	Intermediate Similarity	NPC91693
0.7953	Intermediate Similarity	NPC67251
0.7953	Intermediate Similarity	NPC265557
0.7953	Intermediate Similarity	NPC18945
0.7953	Intermediate Similarity	NPC105926
0.7951	Intermediate Similarity	NPC46269
0.7951	Intermediate Similarity	NPC106395
0.7951	Intermediate Similarity	NPC471204
0.7939	Intermediate Similarity	NPC471855
0.7939	Intermediate Similarity	NPC34963
0.7937	Intermediate Similarity	NPC159456
0.7937	Intermediate Similarity	NPC477046
0.7937	Intermediate Similarity	NPC470779
0.7937	Intermediate Similarity	NPC67569
0.7937	Intermediate Similarity	NPC4021
0.7937	Intermediate Similarity	NPC102822
0.7934	Intermediate Similarity	NPC317107
0.7934	Intermediate Similarity	NPC179798
0.7934	Intermediate Similarity	NPC304180
0.7931	Intermediate Similarity	NPC474742
0.7923	Intermediate Similarity	NPC470880
0.7923	Intermediate Similarity	NPC470851
0.7923	Intermediate Similarity	NPC35109
0.7917	Intermediate Similarity	NPC42662
0.7917	Intermediate Similarity	NPC163004
0.7913	Intermediate Similarity	NPC161855
0.7907	Intermediate Similarity	NPC470882
0.7907	Intermediate Similarity	NPC298841
0.7907	Intermediate Similarity	NPC473253
0.7903	Intermediate Similarity	NPC475809
0.7903	Intermediate Similarity	NPC474654
0.7903	Intermediate Similarity	NPC471146
0.7903	Intermediate Similarity	NPC470854
0.7903	Intermediate Similarity	NPC97908
0.7903	Intermediate Similarity	NPC134430

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 NPC471939 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	1722
0.2-0.3	3575
0.3-0.4	2281
0.4-0.5	882
0.5-0.6	336
0.6-0.7	109
0.7-0.8	11
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
0.7899	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD6371	Approved
0.7686	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5344	Discontinued
0.7619	Intermediate Similarity	NPD7115	Discovery
0.7578	Intermediate Similarity	NPD6319	Approved
0.7542	Intermediate Similarity	NPD6648	Approved
0.744	Intermediate Similarity	NPD8297	Approved
0.7339	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7838	Discovery
0.728	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7319	Approved
0.7252	Intermediate Similarity	NPD8517	Approved
0.7252	Intermediate Similarity	NPD8515	Approved
0.7252	Intermediate Similarity	NPD8513	Phase 3
0.7252	Intermediate Similarity	NPD8516	Approved
0.7244	Intermediate Similarity	NPD4632	Approved
0.7241	Intermediate Similarity	NPD7983	Approved
0.7222	Intermediate Similarity	NPD6649	Approved
0.7222	Intermediate Similarity	NPD6650	Approved
0.7218	Intermediate Similarity	NPD7492	Approved
0.7185	Intermediate Similarity	NPD7736	Approved
0.7176	Intermediate Similarity	NPD6054	Approved
0.7164	Intermediate Similarity	NPD6616	Approved
0.7155	Intermediate Similarity	NPD46	Approved
0.7155	Intermediate Similarity	NPD6698	Approved
0.7121	Intermediate Similarity	NPD6921	Approved
0.712	Intermediate Similarity	NPD6899	Approved
0.712	Intermediate Similarity	NPD6881	Approved
0.7111	Intermediate Similarity	NPD7078	Approved
0.7087	Intermediate Similarity	NPD8130	Phase 1
0.7068	Intermediate Similarity	NPD6370	Approved
0.7063	Intermediate Similarity	NPD6373	Approved
0.7063	Intermediate Similarity	NPD6372	Approved
0.7059	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5697	Approved
0.7037	Intermediate Similarity	NPD7507	Approved
0.7031	Intermediate Similarity	NPD6882	Approved
0.7025	Intermediate Similarity	NPD4225	Approved
0.7015	Intermediate Similarity	NPD7604	Phase 2
0.7015	Intermediate Similarity	NPD8328	Phase 3
0.7008	Intermediate Similarity	NPD4634	Approved
0.7008	Intermediate Similarity	NPD7102	Approved
0.7008	Intermediate Similarity	NPD6883	Approved
0.7008	Intermediate Similarity	NPD7290	Approved
0.6992	Remote Similarity	NPD6015	Approved
0.6992	Remote Similarity	NPD6016	Approved
0.6985	Remote Similarity	NPD8293	Discontinued
0.6985	Remote Similarity	NPD8074	Phase 3
0.696	Remote Similarity	NPD7128	Approved
0.696	Remote Similarity	NPD6402	Approved
0.696	Remote Similarity	NPD6675	Approved
0.696	Remote Similarity	NPD5739	Approved
0.6953	Remote Similarity	NPD6869	Approved
0.6953	Remote Similarity	NPD6847	Approved
0.6953	Remote Similarity	NPD6617	Approved
0.6947	Remote Similarity	NPD6009	Approved
0.694	Remote Similarity	NPD5988	Approved
0.6929	Remote Similarity	NPD6014	Approved
0.6929	Remote Similarity	NPD6012	Approved
0.6929	Remote Similarity	NPD6013	Approved
0.6917	Remote Similarity	NPD6059	Approved
0.6899	Remote Similarity	NPD6053	Discontinued
0.6891	Remote Similarity	NPD5778	Approved
0.6891	Remote Similarity	NPD5779	Approved
0.6866	Remote Similarity	NPD5983	Phase 2
0.685	Remote Similarity	NPD6011	Approved
0.685	Remote Similarity	NPD7320	Approved
0.685	Remote Similarity	NPD6686	Approved
0.6842	Remote Similarity	NPD7516	Approved
0.6825	Remote Similarity	NPD6008	Approved
0.6788	Remote Similarity	NPD6336	Discontinued
0.6786	Remote Similarity	NPD7260	Phase 2
0.6783	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.678	Remote Similarity	NPD1695	Approved
0.6772	Remote Similarity	NPD5701	Approved
0.6767	Remote Similarity	NPD7328	Approved
0.6767	Remote Similarity	NPD7327	Approved
0.6748	Remote Similarity	NPD7638	Approved
0.6748	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD7503	Approved
0.672	Remote Similarity	NPD5211	Phase 2
0.6694	Remote Similarity	NPD5285	Approved
0.6694	Remote Similarity	NPD7640	Approved
0.6694	Remote Similarity	NPD7639	Approved
0.6694	Remote Similarity	NPD5286	Approved
0.6694	Remote Similarity	NPD4696	Approved
0.6692	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD7829	Approved
0.6642	Remote Similarity	NPD7830	Approved
0.6618	Remote Similarity	NPD8378	Approved
0.6618	Remote Similarity	NPD8033	Approved
0.6618	Remote Similarity	NPD8296	Approved
0.6618	Remote Similarity	NPD8335	Approved
0.6618	Remote Similarity	NPD8380	Approved
0.6618	Remote Similarity	NPD8379	Approved
0.6614	Remote Similarity	NPD5141	Approved
0.6593	Remote Similarity	NPD7101	Approved
0.6593	Remote Similarity	NPD7100	Approved
0.6587	Remote Similarity	NPD5224	Approved
0.6587	Remote Similarity	NPD5225	Approved
0.6587	Remote Similarity	NPD5226	Approved
0.6587	Remote Similarity	NPD4633	Approved
0.6565	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5282	Discontinued
0.6547	Remote Similarity	NPD8273	Phase 1
0.6544	Remote Similarity	NPD8294	Approved
0.6544	Remote Similarity	NPD8377	Approved
0.6535	Remote Similarity	NPD5175	Approved
0.6535	Remote Similarity	NPD5174	Approved
0.6532	Remote Similarity	NPD4755	Approved
0.6522	Remote Similarity	NPD7642	Approved
0.6519	Remote Similarity	NPD6335	Approved
0.6508	Remote Similarity	NPD1700	Approved
0.6508	Remote Similarity	NPD5223	Approved
0.65	Remote Similarity	NPD6101	Approved
0.65	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6274	Approved
0.6466	Remote Similarity	NPD8133	Approved
0.6462	Remote Similarity	NPD4729	Approved
0.6462	Remote Similarity	NPD4730	Approved
0.6454	Remote Similarity	NPD6033	Approved
0.6452	Remote Similarity	NPD7839	Suspended
0.6446	Remote Similarity	NPD5785	Approved
0.6444	Remote Similarity	NPD6317	Approved
0.6441	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4700	Approved
0.6412	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6083	Phase 2
0.64	Remote Similarity	NPD6084	Phase 2
0.6397	Remote Similarity	NPD6314	Approved
0.6397	Remote Similarity	NPD6313	Approved
0.6393	Remote Similarity	NPD6411	Approved
0.6393	Remote Similarity	NPD7637	Suspended
0.6389	Remote Similarity	NPD6845	Suspended
0.6377	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5249	Phase 3
0.6364	Remote Similarity	NPD5251	Approved
0.6364	Remote Similarity	NPD5248	Approved
0.6364	Remote Similarity	NPD5250	Approved
0.6364	Remote Similarity	NPD5247	Approved
0.6331	Remote Similarity	NPD8368	Discontinued
0.632	Remote Similarity	NPD5221	Approved
0.632	Remote Similarity	NPD5222	Approved
0.632	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8407	Phase 2
0.6312	Remote Similarity	NPD8451	Approved
0.6308	Remote Similarity	NPD4768	Approved
0.6308	Remote Similarity	NPD4767	Approved
0.6303	Remote Similarity	NPD5363	Approved
0.6287	Remote Similarity	NPD7799	Discontinued
0.6276	Remote Similarity	NPD8338	Approved
0.627	Remote Similarity	NPD5173	Approved
0.627	Remote Similarity	NPD7902	Approved
0.6268	Remote Similarity	NPD8448	Approved
0.626	Remote Similarity	NPD6079	Approved
0.626	Remote Similarity	NPD6412	Phase 2
0.6259	Remote Similarity	NPD6909	Approved
0.6259	Remote Similarity	NPD8444	Approved
0.6259	Remote Similarity	NPD6908	Approved
0.625	Remote Similarity	NPD6868	Approved
0.625	Remote Similarity	NPD5786	Approved
0.6243	Remote Similarity	NPD8434	Phase 2
0.624	Remote Similarity	NPD5695	Phase 3
0.622	Remote Similarity	NPD5696	Approved
0.6212	Remote Similarity	NPD5128	Approved
0.621	Remote Similarity	NPD6399	Phase 3
0.6202	Remote Similarity	NPD7632	Discontinued
0.6194	Remote Similarity	NPD5217	Approved
0.6194	Remote Similarity	NPD5215	Approved
0.6194	Remote Similarity	NPD5216	Approved
0.6194	Remote Similarity	NPD7236	Approved
0.619	Remote Similarity	NPD8415	Approved
0.619	Remote Similarity	NPD4697	Phase 3
0.6167	Remote Similarity	NPD1696	Phase 3
0.6167	Remote Similarity	NPD1694	Approved
0.616	Remote Similarity	NPD7748	Approved
0.6159	Remote Similarity	NPD7641	Discontinued
0.6154	Remote Similarity	NPD4754	Approved
0.6149	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD8392	Approved
0.6138	Remote Similarity	NPD8390	Approved
0.6138	Remote Similarity	NPD8391	Approved
0.6129	Remote Similarity	NPD5281	Approved
0.6129	Remote Similarity	NPD5284	Approved
0.6127	Remote Similarity	NPD8341	Approved
0.6127	Remote Similarity	NPD8299	Approved
0.6127	Remote Similarity	NPD8342	Approved
0.6127	Remote Similarity	NPD8340	Approved
0.6119	Remote Similarity	NPD5169	Approved
0.6119	Remote Similarity	NPD5135	Approved
0.6119	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5210	Approved
0.6111	Remote Similarity	NPD4629	Approved
0.6102	Remote Similarity	NPD5369	Approved
0.6101	Remote Similarity	NPD7239	Suspended
0.6098	Remote Similarity	NPD5328	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