NPASS Compound

Structure

NPC257017 OpenBabel07101718312D 48 51 0 0 1 0 0 0 0 0999 V2000 -11.1631 9.6838 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 -1.7468 -0.9740 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 -10.1766 9.5200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8252 8.5837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8387 8.4199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4873 7.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5009 7.3199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1495 6.3836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1630 6.2198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8116 5.2836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8251 5.1198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1900 5.8922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2035 5.7284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5684 6.5008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5819 6.3370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9468 7.1094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0397 6.9456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3911 6.0093 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 0.7541 2.4778 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 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 -0.8884 -1.4869 0.0000 C 0 0 0 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 0.8884 1.4869 0.0000 C 0 0 1 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 1.3776 5.8455 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 -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 1 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 -0.9033 -2.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0127 6.6179 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 0.8435 -1.5128 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 1.7289 4.9093 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 7 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 37 1 0 0 0 0 6 37 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 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 33 1 0 0 0 0 23 27 2 0 0 0 0 23 32 1 0 0 0 0 24 30 2 0 0 0 0 24 31 1 0 0 0 0 25 30 1 0 0 0 0 25 38 1 0 0 0 0 26 30 1 0 0 0 0 26 47 1 0 0 0 0 27 35 1 0 0 0 0 28 36 1 0 0 0 0 28 39 1 6 0 0 0 29 41 2 0 0 0 0 29 48 1 0 0 0 0 31 34 1 0 0 0 0 31 39 1 6 0 0 0 32 38 1 1 0 0 0 32 39 1 0 0 0 0 33 42 2 0 0 0 0 33 47 1 0 0 0 0 34 37 1 0 0 0 0 34 40 1 1 0 0 0 35 38 1 0 0 0 0 35 43 2 0 0 0 0 36 40 1 1 0 0 0 36 44 1 0 0 0 0 37 40 1 0 0 0 0 38 45 1 1 0 0 0 39 46 1 6 0 0 0 40 48 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	670.44
Volume:	720.673
LogP:	7.38
LogD:	4.573
LogS:	-4.071
# Rotatable Bonds:	20
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.08
Synthetic Accessibility Score:	5.316
Fsp3:	0.775
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:	-4.846
MDCK Permeability:	2.3751728804199956e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.833
Human Intestinal Absorption (HIA):	0.249
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.602
Plasma Protein Binding (PPB):	98.92733001708984%
Volume Distribution (VD):	2.225
Pgp-substrate:	2.9474756717681885%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.34
CYP2C19-substrate:	0.487
CYP2C9-inhibitor:	0.671
CYP2C9-substrate:	0.203
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.016
CYP3A4-inhibitor:	0.956
CYP3A4-substrate:	0.45

ADMET: Excretion

Clearance (CL):	3.397
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.87
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.862
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.151
Carcinogencity:	0.132
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC257017

Natural Product ID:	NPC257017
*Common Name:**	OJSQLQBNCVDSFR-LYGGWFSHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OJSQLQBNCVDSFR-LYGGWFSHSA-N
Standard InCHI:	InChI=1S/C40H62O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-33(42)47-26-30-24-31-34-37(5,6)40(34,48-29(4)41)36(44)28(3)39(31,46)32-23-27(2)35(43)38(32,45)25-30/h14-15,23-24,28,31-32,34,36,44-46H,7-13,16-22,25-26H2,1-6H3/b15-14-/t28-,31+,32-,34-,36-,38-,39-,40-/m1/s1
SMILES:	CCCCCCCC/C=CCCCCCCCC(=O)OCC1=C[C@H]2[C@H]3[C@@](C3(C)C)(OC(=O)C)[C@@H]([C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375793
PubChem CID:	72714534
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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT890	Cell Line	SNU-387	Homo sapiens	IC50	=	1200.0	nM	PMID[457116]

☑ 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 NPC257017 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	256
0.1-0.2	1466
0.2-0.3	4247
0.3-0.4	6986
0.4-0.5	13830
0.5-0.6	8292
0.6-0.7	5986
0.7-0.8	1407
0.8-0.85	104
0.85-0.9	29
0.9-0.95	69
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC162009
0.9735	High Similarity	NPC52839
0.9652	High Similarity	NPC145238
0.9646	High Similarity	NPC471128
0.9646	High Similarity	NPC471126
0.9646	High Similarity	NPC145182
0.9646	High Similarity	NPC157252
0.9643	High Similarity	NPC146280
0.9643	High Similarity	NPC124676
0.9558	High Similarity	NPC22628
0.9558	High Similarity	NPC471108
0.9558	High Similarity	NPC275696
0.9558	High Similarity	NPC5991
0.9558	High Similarity	NPC255081
0.9558	High Similarity	NPC5989
0.9469	High Similarity	NPC472397
0.9469	High Similarity	NPC471125
0.9469	High Similarity	NPC472758
0.9469	High Similarity	NPC171905
0.9397	High Similarity	NPC472399
0.9381	High Similarity	NPC156252
0.9381	High Similarity	NPC10721
0.931	High Similarity	NPC19464
0.9304	High Similarity	NPC472759
0.9304	High Similarity	NPC19336
0.9304	High Similarity	NPC475885
0.9304	High Similarity	NPC185876
0.9304	High Similarity	NPC329080
0.9292	High Similarity	NPC234858
0.9292	High Similarity	NPC154363
0.9292	High Similarity	NPC471127
0.9286	High Similarity	NPC474937
0.9244	High Similarity	NPC270109
0.9231	High Similarity	NPC473802
0.9224	High Similarity	NPC472401
0.9217	High Similarity	NPC156745
0.9217	High Similarity	NPC236918
0.9217	High Similarity	NPC180640
0.9204	High Similarity	NPC472400
0.9204	High Similarity	NPC474872
0.9196	High Similarity	NPC265499
0.9196	High Similarity	NPC101825
0.9196	High Similarity	NPC170212
0.9196	High Similarity	NPC151216
0.9196	High Similarity	NPC221511
0.9196	High Similarity	NPC17138
0.9196	High Similarity	NPC475391
0.9196	High Similarity	NPC215643
0.9196	High Similarity	NPC89227
0.9153	High Similarity	NPC473919
0.9153	High Similarity	NPC473709
0.913	High Similarity	NPC472760
0.9115	High Similarity	NPC71889
0.9115	High Similarity	NPC472757
0.9107	High Similarity	NPC174471
0.9107	High Similarity	NPC474871
0.9107	High Similarity	NPC260786
0.9107	High Similarity	NPC96739
0.9083	High Similarity	NPC236999
0.9076	High Similarity	NPC471939
0.9076	High Similarity	NPC222307
0.9043	High Similarity	NPC153651
0.9	High Similarity	NPC471940
0.8938	High Similarity	NPC158523
0.8938	High Similarity	NPC475937
0.885	High Similarity	NPC153036
0.8761	High Similarity	NPC163004
0.8729	High Similarity	NPC472667
0.871	High Similarity	NPC475139
0.871	High Similarity	NPC180902
0.8621	High Similarity	NPC477091
0.8571	High Similarity	NPC475154
0.8571	High Similarity	NPC100017
0.8571	High Similarity	NPC473548
0.8571	High Similarity	NPC475500
0.8571	High Similarity	NPC182266
0.8571	High Similarity	NPC223356
0.8571	High Similarity	NPC471137
0.8571	High Similarity	NPC471136
0.8548	High Similarity	NPC162495
0.85	High Similarity	NPC143755
0.8438	Intermediate Similarity	NPC68282
0.843	Intermediate Similarity	NPC310511
0.8413	Intermediate Similarity	NPC474508
0.8413	Intermediate Similarity	NPC473485
0.8387	Intermediate Similarity	NPC475273
0.8387	Intermediate Similarity	NPC168849
0.8333	Intermediate Similarity	NPC475606
0.8333	Intermediate Similarity	NPC251564
0.8333	Intermediate Similarity	NPC311554
0.8333	Intermediate Similarity	NPC257457
0.8333	Intermediate Similarity	NPC475314
0.8333	Intermediate Similarity	NPC477189
0.8319	Intermediate Similarity	NPC470793
0.8319	Intermediate Similarity	NPC179626
0.8306	Intermediate Similarity	NPC15095
0.8306	Intermediate Similarity	NPC473635
0.8306	Intermediate Similarity	NPC217901
0.8305	Intermediate Similarity	NPC477126
0.8295	Intermediate Similarity	NPC243902
0.8281	Intermediate Similarity	NPC476823
0.8276	Intermediate Similarity	NPC273433
0.8268	Intermediate Similarity	NPC471855
0.8268	Intermediate Similarity	NPC34963
0.8264	Intermediate Similarity	NPC470186
0.8254	Intermediate Similarity	NPC35109
0.8254	Intermediate Similarity	NPC231529
0.8254	Intermediate Similarity	NPC471407
0.8211	Intermediate Similarity	NPC222688
0.8205	Intermediate Similarity	NPC5103
0.8205	Intermediate Similarity	NPC477103
0.8205	Intermediate Similarity	NPC475563
0.8205	Intermediate Similarity	NPC475134
0.8203	Intermediate Similarity	NPC469673
0.8203	Intermediate Similarity	NPC58029
0.8203	Intermediate Similarity	NPC476111
0.8197	Intermediate Similarity	NPC4548
0.8197	Intermediate Similarity	NPC472004
0.8189	Intermediate Similarity	NPC473838
0.8189	Intermediate Similarity	NPC279478
0.8189	Intermediate Similarity	NPC196921
0.8189	Intermediate Similarity	NPC241935
0.8189	Intermediate Similarity	NPC475389
0.8189	Intermediate Similarity	NPC220757
0.8175	Intermediate Similarity	NPC470850
0.816	Intermediate Similarity	NPC293112
0.8151	Intermediate Similarity	NPC469463
0.8151	Intermediate Similarity	NPC469454
0.8151	Intermediate Similarity	NPC469496
0.8145	Intermediate Similarity	NPC11895
0.8145	Intermediate Similarity	NPC473979
0.8136	Intermediate Similarity	NPC475668
0.8136	Intermediate Similarity	NPC475480
0.8136	Intermediate Similarity	NPC473921
0.812	Intermediate Similarity	NPC42662
0.812	Intermediate Similarity	NPC477102
0.8115	Intermediate Similarity	NPC211093
0.8115	Intermediate Similarity	NPC77689
0.8115	Intermediate Similarity	NPC476529
0.8115	Intermediate Similarity	NPC473636
0.8115	Intermediate Similarity	NPC469380
0.8115	Intermediate Similarity	NPC475775
0.8115	Intermediate Similarity	NPC473839
0.811	Intermediate Similarity	NPC104382
0.811	Intermediate Similarity	NPC470851
0.8103	Intermediate Similarity	NPC187435
0.8103	Intermediate Similarity	NPC67321
0.8099	Intermediate Similarity	NPC296822
0.8099	Intermediate Similarity	NPC473590
0.8099	Intermediate Similarity	NPC471854
0.8087	Intermediate Similarity	NPC474550
0.8087	Intermediate Similarity	NPC473577
0.8087	Intermediate Similarity	NPC475585
0.8083	Intermediate Similarity	NPC73314
0.8083	Intermediate Similarity	NPC138303
0.8083	Intermediate Similarity	NPC178289
0.8083	Intermediate Similarity	NPC67290
0.8083	Intermediate Similarity	NPC133677
0.808	Intermediate Similarity	NPC172154
0.808	Intermediate Similarity	NPC24651
0.808	Intermediate Similarity	NPC81736
0.8067	Intermediate Similarity	NPC152117
0.8067	Intermediate Similarity	NPC317687
0.8067	Intermediate Similarity	NPC473877
0.8067	Intermediate Similarity	NPC474516
0.8067	Intermediate Similarity	NPC234042
0.8067	Intermediate Similarity	NPC470063
0.8065	Intermediate Similarity	NPC23786
0.8065	Intermediate Similarity	NPC170538
0.8065	Intermediate Similarity	NPC470265
0.8051	Intermediate Similarity	NPC257240
0.8049	Intermediate Similarity	NPC109607
0.8049	Intermediate Similarity	NPC48692
0.8049	Intermediate Similarity	NPC107338
0.8047	Intermediate Similarity	NPC471170
0.8034	Intermediate Similarity	NPC476479
0.8034	Intermediate Similarity	NPC469916
0.8034	Intermediate Similarity	NPC472439
0.8033	Intermediate Similarity	NPC251310
0.8031	Intermediate Similarity	NPC476091
0.8031	Intermediate Similarity	NPC476078
0.8017	Intermediate Similarity	NPC474333
0.8017	Intermediate Similarity	NPC328374
0.8017	Intermediate Similarity	NPC176840
0.8017	Intermediate Similarity	NPC270958
0.8017	Intermediate Similarity	NPC475290
0.8017	Intermediate Similarity	NPC96312
0.8017	Intermediate Similarity	NPC471816
0.8017	Intermediate Similarity	NPC270478
0.8017	Intermediate Similarity	NPC251236
0.8017	Intermediate Similarity	NPC40632
0.8017	Intermediate Similarity	NPC148458
0.8016	Intermediate Similarity	NPC470973
0.8	Intermediate Similarity	NPC105926
0.8	Intermediate Similarity	NPC106395
0.8	Intermediate Similarity	NPC61442
0.8	Intermediate Similarity	NPC49451
0.8	Intermediate Similarity	NPC18945
0.8	Intermediate Similarity	NPC471204
0.8	Intermediate Similarity	NPC91693

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 NPC257017 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	1826
0.2-0.3	3614
0.3-0.4	2203
0.4-0.5	851
0.5-0.6	261
0.6-0.7	150
0.7-0.8	18
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8051	Intermediate Similarity	NPD6371	Approved
0.7769	Intermediate Similarity	NPD8297	Approved
0.7731	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD5344	Discontinued
0.7667	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7115	Discovery
0.7647	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6319	Approved
0.7603	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4632	Approved
0.7541	Intermediate Similarity	NPD6649	Approved
0.7541	Intermediate Similarity	NPD6650	Approved
0.7442	Intermediate Similarity	NPD7604	Phase 2
0.7438	Intermediate Similarity	NPD6881	Approved
0.7438	Intermediate Similarity	NPD6899	Approved
0.7398	Intermediate Similarity	NPD8130	Phase 1
0.7377	Intermediate Similarity	NPD6373	Approved
0.7377	Intermediate Similarity	NPD6372	Approved
0.7355	Intermediate Similarity	NPD5697	Approved
0.7355	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6882	Approved
0.7328	Intermediate Similarity	NPD7507	Approved
0.7317	Intermediate Similarity	NPD6883	Approved
0.7317	Intermediate Similarity	NPD7102	Approved
0.7317	Intermediate Similarity	NPD7290	Approved
0.7295	Intermediate Similarity	NPD6686	Approved
0.7293	Intermediate Similarity	NPD7319	Approved
0.7288	Intermediate Similarity	NPD6648	Approved
0.7273	Intermediate Similarity	NPD7128	Approved
0.7273	Intermediate Similarity	NPD6675	Approved
0.7273	Intermediate Similarity	NPD5739	Approved
0.7273	Intermediate Similarity	NPD6402	Approved
0.7266	Intermediate Similarity	NPD7516	Approved
0.7258	Intermediate Similarity	NPD6617	Approved
0.7258	Intermediate Similarity	NPD6869	Approved
0.7258	Intermediate Similarity	NPD6847	Approved
0.7252	Intermediate Similarity	NPD7492	Approved
0.7244	Intermediate Similarity	NPD6009	Approved
0.7236	Intermediate Similarity	NPD6014	Approved
0.7236	Intermediate Similarity	NPD6013	Approved
0.7236	Intermediate Similarity	NPD6012	Approved
0.7218	Intermediate Similarity	NPD7736	Approved
0.7209	Intermediate Similarity	NPD6054	Approved
0.7203	Intermediate Similarity	NPD7638	Approved
0.7203	Intermediate Similarity	NPD4225	Approved
0.7197	Intermediate Similarity	NPD6616	Approved
0.7193	Intermediate Similarity	NPD6698	Approved
0.7193	Intermediate Similarity	NPD46	Approved
0.7188	Intermediate Similarity	NPD7327	Approved
0.7188	Intermediate Similarity	NPD7328	Approved
0.7154	Intermediate Similarity	NPD5983	Phase 2
0.7154	Intermediate Similarity	NPD6921	Approved
0.7154	Intermediate Similarity	NPD7320	Approved
0.7154	Intermediate Similarity	NPD6011	Approved
0.7143	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD7640	Approved
0.7143	Intermediate Similarity	NPD7078	Approved
0.7099	Intermediate Similarity	NPD6370	Approved
0.7073	Intermediate Similarity	NPD5701	Approved
0.7068	Intermediate Similarity	NPD6336	Discontinued
0.7045	Intermediate Similarity	NPD8328	Phase 3
0.7043	Intermediate Similarity	NPD7838	Discovery
0.704	Intermediate Similarity	NPD4634	Approved
0.7025	Intermediate Similarity	NPD5211	Phase 2
0.7023	Intermediate Similarity	NPD6015	Approved
0.7023	Intermediate Similarity	NPD6016	Approved
0.7023	Intermediate Similarity	NPD8380	Approved
0.7023	Intermediate Similarity	NPD8378	Approved
0.7023	Intermediate Similarity	NPD8379	Approved
0.7023	Intermediate Similarity	NPD8033	Approved
0.7023	Intermediate Similarity	NPD8296	Approved
0.7023	Intermediate Similarity	NPD8335	Approved
0.7015	Intermediate Similarity	NPD8293	Discontinued
0.7	Intermediate Similarity	NPD4696	Approved
0.7	Intermediate Similarity	NPD5286	Approved
0.7	Intermediate Similarity	NPD5285	Approved
0.6992	Remote Similarity	NPD6008	Approved
0.697	Remote Similarity	NPD5988	Approved
0.6949	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8294	Approved
0.6947	Remote Similarity	NPD6059	Approved
0.6947	Remote Similarity	NPD8377	Approved
0.6929	Remote Similarity	NPD6053	Discontinued
0.6911	Remote Similarity	NPD5141	Approved
0.6894	Remote Similarity	NPD7503	Approved
0.6885	Remote Similarity	NPD5226	Approved
0.6885	Remote Similarity	NPD5224	Approved
0.6885	Remote Similarity	NPD5225	Approved
0.6885	Remote Similarity	NPD4633	Approved
0.6875	Remote Similarity	NPD8133	Approved
0.687	Remote Similarity	NPD7101	Approved
0.687	Remote Similarity	NPD7100	Approved
0.685	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.685	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6084	Phase 2
0.6833	Remote Similarity	NPD4755	Approved
0.6833	Remote Similarity	NPD6083	Phase 2
0.6829	Remote Similarity	NPD5174	Approved
0.6829	Remote Similarity	NPD5175	Approved
0.6825	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7260	Phase 2
0.6803	Remote Similarity	NPD5223	Approved
0.6794	Remote Similarity	NPD6335	Approved
0.6769	Remote Similarity	NPD6274	Approved
0.6767	Remote Similarity	NPD8515	Approved
0.6767	Remote Similarity	NPD8513	Phase 3
0.6767	Remote Similarity	NPD8516	Approved
0.6767	Remote Similarity	NPD8517	Approved
0.6746	Remote Similarity	NPD4730	Approved
0.6746	Remote Similarity	NPD4729	Approved
0.6723	Remote Similarity	NPD5282	Discontinued
0.6721	Remote Similarity	NPD4700	Approved
0.6718	Remote Similarity	NPD6317	Approved
0.6718	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7983	Approved
0.6694	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6313	Approved
0.6642	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5250	Approved
0.6641	Remote Similarity	NPD5251	Approved
0.6641	Remote Similarity	NPD5248	Approved
0.6641	Remote Similarity	NPD5249	Phase 3
0.6641	Remote Similarity	NPD5247	Approved
0.6639	Remote Similarity	NPD6399	Phase 3
0.6639	Remote Similarity	NPD5696	Approved
0.6639	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7632	Discontinued
0.6612	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5222	Approved
0.6612	Remote Similarity	NPD5221	Approved
0.661	Remote Similarity	NPD5785	Approved
0.6609	Remote Similarity	NPD1694	Approved
0.6587	Remote Similarity	NPD4767	Approved
0.6587	Remote Similarity	NPD4768	Approved
0.6583	Remote Similarity	NPD7748	Approved
0.6557	Remote Similarity	NPD5173	Approved
0.6555	Remote Similarity	NPD6079	Approved
0.6529	Remote Similarity	NPD5210	Approved
0.6529	Remote Similarity	NPD4629	Approved
0.6529	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8074	Phase 3
0.6519	Remote Similarity	NPD6909	Approved
0.6519	Remote Similarity	NPD6908	Approved
0.6515	Remote Similarity	NPD6868	Approved
0.6484	Remote Similarity	NPD5128	Approved
0.6475	Remote Similarity	NPD4697	Phase 3
0.6475	Remote Similarity	NPD6033	Approved
0.6466	Remote Similarity	NPD1696	Phase 3
0.6462	Remote Similarity	NPD5215	Approved
0.6462	Remote Similarity	NPD5217	Approved
0.6462	Remote Similarity	NPD5216	Approved
0.6446	Remote Similarity	NPD7900	Approved
0.6446	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4754	Approved
0.6417	Remote Similarity	NPD5693	Phase 1
0.6417	Remote Similarity	NPD7515	Phase 2
0.6408	Remote Similarity	NPD6845	Suspended
0.64	Remote Similarity	NPD1700	Approved
0.6387	Remote Similarity	NPD4753	Phase 2
0.6387	Remote Similarity	NPD5328	Approved
0.6385	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD5135	Approved
0.6385	Remote Similarity	NPD5169	Approved
0.6364	Remote Similarity	NPD5778	Approved
0.6364	Remote Similarity	NPD5779	Approved
0.6364	Remote Similarity	NPD4202	Approved
0.6348	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD5127	Approved
0.6325	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6672	Approved
0.6303	Remote Similarity	NPD5737	Approved
0.6294	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5281	Approved
0.6281	Remote Similarity	NPD5284	Approved
0.6281	Remote Similarity	NPD7637	Suspended
0.6281	Remote Similarity	NPD8035	Phase 2
0.6281	Remote Similarity	NPD8034	Phase 2
0.6271	Remote Similarity	NPD3618	Phase 1
0.625	Remote Similarity	NPD6904	Approved
0.625	Remote Similarity	NPD6080	Approved
0.625	Remote Similarity	NPD6673	Approved
0.6218	Remote Similarity	NPD7524	Approved
0.6218	Remote Similarity	NPD3573	Approved
0.6209	Remote Similarity	NPD7236	Approved
0.6194	Remote Similarity	NPD5167	Approved
0.6187	Remote Similarity	NPD7642	Approved
0.6186	Remote Similarity	NPD5363	Approved
0.6181	Remote Similarity	NPD8338	Approved
0.6179	Remote Similarity	NPD6001	Approved
0.6154	Remote Similarity	NPD5362	Discontinued
0.6154	Remote Similarity	NPD5956	Approved
0.6154	Remote Similarity	NPD6110	Phase 1
0.6154	Remote Similarity	NPD8368	Discontinued
0.6154	Remote Similarity	NPD7154	Phase 3
0.6148	Remote Similarity	NPD6050	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