NPASS Compound

Structure

NPC124676 OpenBabel07101718182D 47 50 0 0 1 0 0 0 0 0999 V2000 -10.9719 14.7869 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 -10.3368 14.0145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6882 13.0782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0531 12.3058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4045 11.3696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7693 10.5972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1207 9.6609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4856 8.8885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8370 7.9523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2019 7.1799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2154 7.3437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5802 6.5713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5938 6.7351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9586 5.9627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9722 6.1265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3370 5.3541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3505 5.5179 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 -0.7541 2.4778 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 -2.9921 2.2764 0.0000 C 0 0 2 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 -2.7154 4.7455 0.0000 C 0 0 0 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 -0.0150 0.9999 0.0000 C 0 0 2 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 -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 0.9033 -2.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0668 3.8092 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 -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 38 1 0 0 0 0 6 38 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 34 1 0 0 0 0 23 27 2 0 0 0 0 23 32 1 0 0 0 0 24 30 1 0 0 0 0 25 30 2 0 0 0 0 25 33 1 0 0 0 0 26 30 1 0 0 0 0 26 46 1 0 0 0 0 27 35 1 0 0 0 0 28 37 1 0 0 0 0 28 39 1 1 0 0 0 29 41 2 0 0 0 0 29 47 1 0 0 0 0 31 24 1 6 0 0 0 31 32 1 0 0 0 0 31 35 1 0 0 0 0 32 39 1 6 0 0 0 33 36 1 0 0 0 0 33 39 1 1 0 0 0 34 42 2 0 0 0 0 34 46 1 0 0 0 0 35 43 2 0 0 0 0 36 38 1 0 0 0 0 36 40 1 6 0 0 0 37 40 1 6 0 0 0 37 44 1 0 0 0 0 38 40 1 0 0 0 0 39 45 1 1 0 0 0 40 47 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	654.45
Volume:	711.883
LogP:	7.584
LogD:	4.682
LogS:	-4.403
# Rotatable Bonds:	20
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.087
Synthetic Accessibility Score:	5.156
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:	-4.928
MDCK Permeability:	2.3140473786043003e-05
Pgp-inhibitor:	0.943
Pgp-substrate:	0.195
Human Intestinal Absorption (HIA):	0.155
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.594
Plasma Protein Binding (PPB):	100.35640716552734%
Volume Distribution (VD):	2.183
Pgp-substrate:	1.2525581121444702%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.362
CYP2C19-substrate:	0.115
CYP2C9-inhibitor:	0.386
CYP2C9-substrate:	0.288
CYP2D6-inhibitor:	0.223
CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.924
CYP3A4-substrate:	0.43

ADMET: Excretion

Clearance (CL):	3.898
Half-life (T1/2):	0.196

ADMET: Toxicity

hERG Blockers:	0.293
Human Hepatotoxicity (H-HT):	0.289
Drug-inuced Liver Injury (DILI):	0.924
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.192
Maximum Recommended Daily Dose:	0.659
Skin Sensitization:	0.814
Carcinogencity:	0.255
Eye Corrosion:	0.003
Eye Irritation:	0.008
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: NPC124676

Natural Product ID:	NPC124676
*Common Name:**	CUEBPOLGBRSPMP-WIVYDGDASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CUEBPOLGBRSPMP-WIVYDGDASA-N
Standard InCHI:	InChI=1S/C40H62O7/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-34(42)46-26-30-24-31-32(23-27(2)35(31)43)39(45)28(3)37(44)40(47-29(4)41)36(33(39)25-30)38(40,5)6/h14-15,23,25,28,31-33,36-37,44-45H,7-13,16-22,24,26H2,1-6H3/b15-14-/t28-,31-,32-,33+,36-,37-,39+,40-/m1/s1
SMILES:	CCCCCCCC/C=CCCCCCCCC(=O)OCC1=C[C@H]2[C@@H]3C(C)(C)[C@@]3([C@@H]([C@@H](C)[C@@]2([C@@H]2C=C(C)C(=O)[C@@H]2C1)O)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375791
PubChem CID:	73354873
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

*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	=	6600.0	nM	PMID[531291]

☑ 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 NPC124676 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	239
0.1-0.2	1421
0.2-0.3	4158
0.3-0.4	6738
0.4-0.5	13833
0.5-0.6	8168
0.6-0.7	6397
0.7-0.8	1509
0.8-0.85	116
0.85-0.9	35
0.9-0.95	59
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC146280
0.9725	High Similarity	NPC10721
0.9643	High Similarity	NPC162009
0.9643	High Similarity	NPC257017
0.964	High Similarity	NPC475885
0.964	High Similarity	NPC472759
0.964	High Similarity	NPC329080
0.9633	High Similarity	NPC154363
0.9633	High Similarity	NPC471127
0.9633	High Similarity	NPC234858
0.955	High Similarity	NPC156745
0.955	High Similarity	NPC236918
0.9541	High Similarity	NPC472400
0.945	High Similarity	NPC472757
0.9381	High Similarity	NPC52839
0.9304	High Similarity	NPC145238
0.9292	High Similarity	NPC471128
0.9292	High Similarity	NPC471126
0.9292	High Similarity	NPC157252
0.9292	High Similarity	NPC145182
0.9204	High Similarity	NPC5991
0.9204	High Similarity	NPC471108
0.9204	High Similarity	NPC255081
0.9204	High Similarity	NPC275696
0.9204	High Similarity	NPC22628
0.9204	High Similarity	NPC5989
0.9196	High Similarity	NPC156252
0.9115	High Similarity	NPC472758
0.9115	High Similarity	NPC472397
0.9115	High Similarity	NPC471125
0.9115	High Similarity	NPC171905
0.9052	High Similarity	NPC472399
0.9009	High Similarity	NPC17138
0.9009	High Similarity	NPC170212
0.9009	High Similarity	NPC215643
0.9009	High Similarity	NPC89227
0.9009	High Similarity	NPC265499
0.9009	High Similarity	NPC101825
0.9009	High Similarity	NPC151216
0.9009	High Similarity	NPC221511
0.8966	High Similarity	NPC19464
0.8957	High Similarity	NPC185876
0.8957	High Similarity	NPC19336
0.8947	High Similarity	NPC472760
0.8929	High Similarity	NPC71889
0.8929	High Similarity	NPC474937
0.8919	High Similarity	NPC474871
0.8919	High Similarity	NPC174471
0.8919	High Similarity	NPC260786
0.8919	High Similarity	NPC96739
0.8908	High Similarity	NPC270109
0.8889	High Similarity	NPC473802
0.8879	High Similarity	NPC472401
0.887	High Similarity	NPC180640
0.885	High Similarity	NPC474872
0.8839	High Similarity	NPC475391
0.8814	High Similarity	NPC473919
0.8814	High Similarity	NPC473709
0.875	High Similarity	NPC158523
0.875	High Similarity	NPC236999
0.875	High Similarity	NPC475937
0.8739	High Similarity	NPC471939
0.8739	High Similarity	NPC222307
0.8707	High Similarity	NPC472667
0.8696	High Similarity	NPC153651
0.8667	High Similarity	NPC471940
0.8661	High Similarity	NPC153036
0.8571	High Similarity	NPC163004
0.8475	Intermediate Similarity	NPC143755
0.8468	Intermediate Similarity	NPC476111
0.8435	Intermediate Similarity	NPC477091
0.843	Intermediate Similarity	NPC473635
0.843	Intermediate Similarity	NPC293112
0.8417	Intermediate Similarity	NPC11895
0.8407	Intermediate Similarity	NPC273433
0.8403	Intermediate Similarity	NPC310511
0.8393	Intermediate Similarity	NPC67321
0.8393	Intermediate Similarity	NPC187435
0.839	Intermediate Similarity	NPC470186
0.8387	Intermediate Similarity	NPC180902
0.8387	Intermediate Similarity	NPC475139
0.8348	Intermediate Similarity	NPC152117
0.8348	Intermediate Similarity	NPC234042
0.8348	Intermediate Similarity	NPC470063
0.8333	Intermediate Similarity	NPC170538
0.8291	Intermediate Similarity	NPC470793
0.8291	Intermediate Similarity	NPC179626
0.8291	Intermediate Similarity	NPC471816
0.8264	Intermediate Similarity	NPC469789
0.8264	Intermediate Similarity	NPC473979
0.8261	Intermediate Similarity	NPC474846
0.8261	Intermediate Similarity	NPC469655
0.8261	Intermediate Similarity	NPC469656
0.8261	Intermediate Similarity	NPC470076
0.8254	Intermediate Similarity	NPC471137
0.8254	Intermediate Similarity	NPC471136
0.8254	Intermediate Similarity	NPC473548
0.8254	Intermediate Similarity	NPC223356
0.8254	Intermediate Similarity	NPC182266
0.8254	Intermediate Similarity	NPC100017
0.8254	Intermediate Similarity	NPC475154
0.8254	Intermediate Similarity	NPC475500
0.825	Intermediate Similarity	NPC67569
0.8246	Intermediate Similarity	NPC5475
0.8246	Intermediate Similarity	NPC173905
0.8246	Intermediate Similarity	NPC472216
0.8246	Intermediate Similarity	NPC284828
0.824	Intermediate Similarity	NPC189393
0.824	Intermediate Similarity	NPC90814
0.8235	Intermediate Similarity	NPC473636
0.8235	Intermediate Similarity	NPC211093
0.8235	Intermediate Similarity	NPC77689
0.8235	Intermediate Similarity	NPC469380
0.8235	Intermediate Similarity	NPC473839
0.8226	Intermediate Similarity	NPC162495
0.8226	Intermediate Similarity	NPC231529
0.822	Intermediate Similarity	NPC475323
0.822	Intermediate Similarity	NPC469684
0.822	Intermediate Similarity	NPC284068
0.8205	Intermediate Similarity	NPC133677
0.8205	Intermediate Similarity	NPC138303
0.8205	Intermediate Similarity	NPC67290
0.8205	Intermediate Similarity	NPC73314
0.8198	Intermediate Similarity	NPC476081
0.8197	Intermediate Similarity	NPC81736
0.8197	Intermediate Similarity	NPC172154
0.819	Intermediate Similarity	NPC472002
0.8182	Intermediate Similarity	NPC23786
0.8182	Intermediate Similarity	NPC470265
0.8174	Intermediate Similarity	NPC5103
0.8174	Intermediate Similarity	NPC472214
0.8174	Intermediate Similarity	NPC472215
0.8174	Intermediate Similarity	NPC257240
0.8174	Intermediate Similarity	NPC477103
0.8174	Intermediate Similarity	NPC253906
0.8167	Intermediate Similarity	NPC4548
0.8167	Intermediate Similarity	NPC48692
0.8158	Intermediate Similarity	NPC306265
0.8158	Intermediate Similarity	NPC472439
0.8158	Intermediate Similarity	NPC469916
0.8151	Intermediate Similarity	NPC284707
0.8145	Intermediate Similarity	NPC470850
0.8136	Intermediate Similarity	NPC176840
0.8125	Intermediate Similarity	NPC68282
0.8125	Intermediate Similarity	NPC61442
0.812	Intermediate Similarity	NPC477126
0.812	Intermediate Similarity	NPC469463
0.812	Intermediate Similarity	NPC469496
0.812	Intermediate Similarity	NPC471204
0.812	Intermediate Similarity	NPC469454
0.812	Intermediate Similarity	NPC46269
0.812	Intermediate Similarity	NPC106395
0.8115	Intermediate Similarity	NPC469352
0.8095	Intermediate Similarity	NPC473485
0.8095	Intermediate Similarity	NPC474508
0.8087	Intermediate Similarity	NPC469370
0.8087	Intermediate Similarity	NPC477102
0.8083	Intermediate Similarity	NPC475041
0.808	Intermediate Similarity	NPC104382
0.808	Intermediate Similarity	NPC470851
0.807	Intermediate Similarity	NPC143609
0.8067	Intermediate Similarity	NPC98249
0.8067	Intermediate Similarity	NPC473656
0.8067	Intermediate Similarity	NPC475809
0.8067	Intermediate Similarity	NPC134430
0.8067	Intermediate Similarity	NPC53396
0.8067	Intermediate Similarity	NPC470493
0.8067	Intermediate Similarity	NPC13713
0.8067	Intermediate Similarity	NPC58662
0.8067	Intermediate Similarity	NPC312824
0.8067	Intermediate Similarity	NPC183580
0.8065	Intermediate Similarity	NPC168849
0.8065	Intermediate Similarity	NPC475273
0.8053	Intermediate Similarity	NPC118911
0.8053	Intermediate Similarity	NPC475585
0.8053	Intermediate Similarity	NPC474550
0.8053	Intermediate Similarity	NPC473577
0.8051	Intermediate Similarity	NPC238667
0.8049	Intermediate Similarity	NPC8369
0.8036	Intermediate Similarity	NPC472552
0.8036	Intermediate Similarity	NPC162973
0.8036	Intermediate Similarity	NPC474709
0.8034	Intermediate Similarity	NPC269530
0.8034	Intermediate Similarity	NPC236217
0.8034	Intermediate Similarity	NPC76550
0.8034	Intermediate Similarity	NPC138757
0.8034	Intermediate Similarity	NPC476801
0.8034	Intermediate Similarity	NPC123855
0.8018	Intermediate Similarity	NPC47024
0.8017	Intermediate Similarity	NPC79579
0.8017	Intermediate Similarity	NPC5284
0.8017	Intermediate Similarity	NPC268530
0.8017	Intermediate Similarity	NPC475563
0.8017	Intermediate Similarity	NPC475003
0.8017	Intermediate Similarity	NPC476961
0.8017	Intermediate Similarity	NPC154491
0.8017	Intermediate Similarity	NPC251226
0.8017	Intermediate Similarity	NPC475134
0.8016	Intermediate Similarity	NPC475314
0.8016	Intermediate Similarity	NPC251564

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 NPC124676 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	1771
0.2-0.3	3601
0.3-0.4	2248
0.4-0.5	880
0.5-0.6	274
0.6-0.7	148
0.7-0.8	12
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
0.8174	Intermediate Similarity	NPD6371	Approved
0.7946	Intermediate Similarity	NPD5344	Discontinued
0.7931	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7115	Discovery
0.7712	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6648	Approved
0.7458	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD4225	Approved
0.7438	Intermediate Similarity	NPD8297	Approved
0.7395	Intermediate Similarity	NPD6686	Approved
0.7377	Intermediate Similarity	NPD4632	Approved
0.7311	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7638	Approved
0.7302	Intermediate Similarity	NPD6319	Approved
0.7297	Intermediate Similarity	NPD6698	Approved
0.7297	Intermediate Similarity	NPD46	Approved
0.7287	Intermediate Similarity	NPD7507	Approved
0.7266	Intermediate Similarity	NPD7604	Phase 2
0.7252	Intermediate Similarity	NPD7319	Approved
0.725	Intermediate Similarity	NPD6881	Approved
0.725	Intermediate Similarity	NPD6899	Approved
0.7241	Intermediate Similarity	NPD7640	Approved
0.7241	Intermediate Similarity	NPD7639	Approved
0.7222	Intermediate Similarity	NPD7516	Approved
0.7213	Intermediate Similarity	NPD8130	Phase 1
0.7213	Intermediate Similarity	NPD6650	Approved
0.7213	Intermediate Similarity	NPD6649	Approved
0.7193	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD7838	Discovery
0.7143	Intermediate Similarity	NPD7328	Approved
0.7143	Intermediate Similarity	NPD7327	Approved
0.7131	Intermediate Similarity	NPD6883	Approved
0.7131	Intermediate Similarity	NPD7102	Approved
0.7131	Intermediate Similarity	NPD7290	Approved
0.7083	Intermediate Similarity	NPD6402	Approved
0.7083	Intermediate Similarity	NPD6008	Approved
0.7083	Intermediate Similarity	NPD5739	Approved
0.7083	Intermediate Similarity	NPD7128	Approved
0.7083	Intermediate Similarity	NPD6675	Approved
0.7077	Intermediate Similarity	NPD7492	Approved
0.7073	Intermediate Similarity	NPD6617	Approved
0.7073	Intermediate Similarity	NPD6869	Approved
0.7073	Intermediate Similarity	NPD6847	Approved
0.7063	Intermediate Similarity	NPD6009	Approved
0.7049	Intermediate Similarity	NPD6372	Approved
0.7049	Intermediate Similarity	NPD6014	Approved
0.7049	Intermediate Similarity	NPD6012	Approved
0.7049	Intermediate Similarity	NPD6013	Approved
0.7049	Intermediate Similarity	NPD6373	Approved
0.7045	Intermediate Similarity	NPD7736	Approved
0.7031	Intermediate Similarity	NPD6054	Approved
0.7023	Intermediate Similarity	NPD6616	Approved
0.7016	Intermediate Similarity	NPD6053	Discontinued
0.7016	Intermediate Similarity	NPD6882	Approved
0.6977	Remote Similarity	NPD8379	Approved
0.6977	Remote Similarity	NPD8296	Approved
0.6977	Remote Similarity	NPD6921	Approved
0.6977	Remote Similarity	NPD8378	Approved
0.6977	Remote Similarity	NPD8335	Approved
0.6977	Remote Similarity	NPD5983	Phase 2
0.6977	Remote Similarity	NPD8380	Approved
0.6977	Remote Similarity	NPD8033	Approved
0.697	Remote Similarity	NPD7078	Approved
0.6967	Remote Similarity	NPD6011	Approved
0.6967	Remote Similarity	NPD7320	Approved
0.6923	Remote Similarity	NPD6370	Approved
0.6923	Remote Similarity	NPD7902	Approved
0.6911	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD8377	Approved
0.6899	Remote Similarity	NPD8294	Approved
0.6894	Remote Similarity	NPD6336	Discontinued
0.6885	Remote Similarity	NPD5701	Approved
0.687	Remote Similarity	NPD6399	Phase 3
0.687	Remote Similarity	NPD8328	Phase 3
0.6855	Remote Similarity	NPD4634	Approved
0.6847	Remote Similarity	NPD1694	Approved
0.6846	Remote Similarity	NPD8513	Phase 3
0.6846	Remote Similarity	NPD8517	Approved
0.6846	Remote Similarity	NPD7503	Approved
0.6846	Remote Similarity	NPD8515	Approved
0.6846	Remote Similarity	NPD6015	Approved
0.6846	Remote Similarity	NPD8516	Approved
0.6846	Remote Similarity	NPD6016	Approved
0.6842	Remote Similarity	NPD8293	Discontinued
0.6833	Remote Similarity	NPD5211	Phase 2
0.6825	Remote Similarity	NPD8133	Approved
0.681	Remote Similarity	NPD7748	Approved
0.6807	Remote Similarity	NPD5286	Approved
0.6807	Remote Similarity	NPD4696	Approved
0.6807	Remote Similarity	NPD5285	Approved
0.6794	Remote Similarity	NPD5988	Approved
0.6783	Remote Similarity	NPD7983	Approved
0.6783	Remote Similarity	NPD6079	Approved
0.6769	Remote Similarity	NPD6059	Approved
0.6754	Remote Similarity	NPD1695	Approved
0.6748	Remote Similarity	NPD6412	Phase 2
0.6723	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5141	Approved
0.6696	Remote Similarity	NPD5785	Approved
0.6694	Remote Similarity	NPD5225	Approved
0.6694	Remote Similarity	NPD5224	Approved
0.6694	Remote Similarity	NPD7632	Discontinued
0.6694	Remote Similarity	NPD5226	Approved
0.6694	Remote Similarity	NPD4633	Approved
0.6692	Remote Similarity	NPD7100	Approved
0.6692	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD7900	Approved
0.6642	Remote Similarity	NPD7260	Phase 2
0.6639	Remote Similarity	NPD6083	Phase 2
0.6639	Remote Similarity	NPD5174	Approved
0.6639	Remote Similarity	NPD4755	Approved
0.6639	Remote Similarity	NPD5175	Approved
0.6639	Remote Similarity	NPD6084	Phase 2
0.6638	Remote Similarity	NPD7515	Phase 2
0.6615	Remote Similarity	NPD6335	Approved
0.6612	Remote Similarity	NPD5223	Approved
0.661	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5328	Approved
0.6593	Remote Similarity	NPD8074	Phase 3
0.6589	Remote Similarity	NPD6274	Approved
0.6581	Remote Similarity	NPD5779	Approved
0.6581	Remote Similarity	NPD5778	Approved
0.6577	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5221	Approved
0.6555	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5222	Approved
0.6549	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6317	Approved
0.6538	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4700	Approved
0.65	Remote Similarity	NPD5173	Approved
0.6496	Remote Similarity	NPD8034	Phase 2
0.6496	Remote Similarity	NPD7637	Suspended
0.6496	Remote Similarity	NPD8035	Phase 2
0.6491	Remote Similarity	NPD3618	Phase 1
0.6489	Remote Similarity	NPD6313	Approved
0.6489	Remote Similarity	NPD6314	Approved
0.6471	Remote Similarity	NPD5695	Phase 3
0.6466	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6868	Approved
0.6446	Remote Similarity	NPD5696	Approved
0.6441	Remote Similarity	NPD4202	Approved
0.6435	Remote Similarity	NPD3573	Approved
0.6435	Remote Similarity	NPD7524	Approved
0.6429	Remote Similarity	NPD4729	Approved
0.6429	Remote Similarity	NPD4730	Approved
0.6417	Remote Similarity	NPD4697	Phase 3
0.6404	Remote Similarity	NPD1696	Phase 3
0.6356	Remote Similarity	NPD6411	Approved
0.6356	Remote Similarity	NPD5281	Approved
0.6356	Remote Similarity	NPD5284	Approved
0.6343	Remote Similarity	NPD6909	Approved
0.6343	Remote Similarity	NPD6908	Approved
0.6333	Remote Similarity	NPD4629	Approved
0.6333	Remote Similarity	NPD5210	Approved
0.6328	Remote Similarity	NPD5247	Approved
0.6328	Remote Similarity	NPD5248	Approved
0.6328	Remote Similarity	NPD5250	Approved
0.6328	Remote Similarity	NPD5251	Approved
0.6328	Remote Similarity	NPD5249	Phase 3
0.6316	Remote Similarity	NPD4786	Approved
0.6304	Remote Similarity	NPD6033	Approved
0.6299	Remote Similarity	NPD5128	Approved
0.6283	Remote Similarity	NPD5209	Approved
0.6279	Remote Similarity	NPD5217	Approved
0.6279	Remote Similarity	NPD5215	Approved
0.6279	Remote Similarity	NPD5216	Approved
0.627	Remote Similarity	NPD4767	Approved
0.627	Remote Similarity	NPD4768	Approved
0.6261	Remote Similarity	NPD5363	Approved
0.625	Remote Similarity	NPD7642	Approved
0.625	Remote Similarity	NPD6001	Approved
0.6241	Remote Similarity	NPD6845	Suspended
0.624	Remote Similarity	NPD4754	Approved
0.6239	Remote Similarity	NPD6672	Approved
0.6239	Remote Similarity	NPD5737	Approved
0.6228	Remote Similarity	NPD7154	Phase 3
0.6228	Remote Similarity	NPD5362	Discontinued
0.6218	Remote Similarity	NPD5693	Phase 1
0.6216	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.621	Remote Similarity	NPD1700	Approved
0.6207	Remote Similarity	NPD5330	Approved
0.6207	Remote Similarity	NPD6409	Approved
0.6207	Remote Similarity	NPD7521	Approved
0.6207	Remote Similarity	NPD7146	Approved
0.6207	Remote Similarity	NPD7334	Approved
0.6207	Remote Similarity	NPD6684	Approved
0.6202	Remote Similarity	NPD5169	Approved
0.6202	Remote Similarity	NPD5135	Approved
0.6202	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6101	Approved
0.6186	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4753	Phase 2
0.6181	Remote Similarity	NPD7966	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