NPASS Compound

Structure

NPC471606 OpenBabel07101718202D 65 71 0 0 1 0 0 0 0 0999 V2000 -4.3333 4.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1246 0.5598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8370 3.1239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5038 3.1594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5782 3.2812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2598 0.8625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3604 -5.3408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9167 -1.7033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2696 3.0841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2229 -4.9836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6197 -4.7725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1760 -1.1349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7948 -2.6289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9123 2.2216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7013 3.8248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3447 -4.0580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7415 -3.8469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3135 -1.4922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9323 -2.9861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9867 2.0997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7757 3.7029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1223 2.5315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8085 -1.4004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1054 1.4127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9336 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6906 3.2721 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.4769 1.2322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0787 2.2221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6041 -3.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1916 -2.4178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4184 2.8404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7476 0.9922 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6170 -0.9336 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9336 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4795 1.6690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7440 1.9519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7259 -2.5640 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9853 -1.9957 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9856 1.0501 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8085 0.4668 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5188 0.2416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5669 1.3686 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3291 -2.7751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4928 2.7185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1071 -1.0701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9355 2.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6170 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0337 2.1771 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5885 -2.2068 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.6162 3.1503 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9804 1.9804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4255 -1.4004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4051 1.5471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1227 -2.3530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0871 -0.4990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2073 -3.7007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9245 3.4592 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9696 -0.7128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7016 3.0496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9336 -0.9336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6258 0.0666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9112 0.9283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1355 1.8560 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2416 0.9018 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 46 1 0 0 0 0 5 46 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 14 20 1 0 0 0 0 15 21 2 0 0 0 0 16 29 2 0 0 0 0 17 29 1 0 0 0 0 18 30 2 0 0 0 0 19 30 1 0 0 0 0 20 31 2 0 0 0 0 21 31 1 0 0 0 0 22 26 1 0 0 0 0 22 35 1 0 0 0 0 23 33 1 0 0 0 0 23 34 1 0 0 0 0 24 32 1 0 0 0 0 24 49 1 0 0 0 0 25 48 1 0 0 0 0 25 61 1 0 0 0 0 26 51 1 0 0 0 0 27 32 1 0 0 0 0 27 36 2 0 0 0 0 28 52 2 0 0 0 0 28 65 1 0 0 0 0 29 37 1 0 0 0 0 30 43 1 0 0 0 0 31 44 1 0 0 0 0 32 62 1 6 0 0 0 33 47 1 6 0 0 0 33 53 1 0 0 0 0 34 48 1 6 0 0 0 34 61 1 0 0 0 0 35 54 2 0 0 0 0 35 63 1 0 0 0 0 36 39 1 0 0 0 0 36 46 1 0 0 0 0 37 38 1 0 0 0 0 37 50 1 6 0 0 0 38 45 1 0 0 0 0 38 55 1 6 0 0 0 39 41 1 0 0 0 0 39 63 1 6 0 0 0 40 42 1 0 0 0 0 40 47 1 6 0 0 0 40 48 1 0 0 0 0 41 47 1 0 0 0 0 41 56 2 0 0 0 0 42 49 1 1 0 0 0 42 64 1 0 0 0 0 43 50 2 3 0 0 0 43 57 1 0 0 0 0 44 58 2 0 0 0 0 44 64 1 0 0 0 0 45 59 2 0 0 0 0 45 62 1 0 0 0 0 46 49 1 0 0 0 0 47 6 1 6 0 0 0 48 65 1 1 0 0 0 49 60 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	897.36
Volume:	896.831
LogP:	3.649
LogD:	2.445
LogS:	-4.319
# Rotatable Bonds:	17
TPSA:	241.52
# H-Bond Aceptor:	16
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.129
Synthetic Accessibility Score:	6.232
Fsp3:	0.469
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:	-5.538
MDCK Permeability:	6.331151234917343e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.295
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125
Plasma Protein Binding (PPB):	94.23258209228516%
Volume Distribution (VD):	0.559
Pgp-substrate:	6.145824909210205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.021
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.64
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.809
CYP3A4-substrate:	0.743

ADMET: Excretion

Clearance (CL):	5.397
Half-life (T1/2):	0.04

ADMET: Toxicity

hERG Blockers:	0.185
Human Hepatotoxicity (H-HT):	0.913
Drug-inuced Liver Injury (DILI):	0.909
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.519
Maximum Recommended Daily Dose:	0.874
Skin Sensitization:	0.05
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC471606

Natural Product ID:	NPC471606
*Common Name:**	YHFPPEJTHPISLW-ROBCKNCGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YHFPPEJTHPISLW-ROBCKNCGSA-N
Standard InCHI:	InChI=1S/C49H55NO15/c1-26(51)22-35(54)63-39-36-27(2)32(62-45(59)38(55)37(29-16-10-7-11-17-29)50-43(57)30-18-12-8-13-19-30)24-49(60,46(36,4)5)42(64-44(58)31-20-14-9-15-21-31)40-47(6,41(39)56)33(53)23-34-48(40,25-61-34)65-28(3)52/h7-21,26,32-34,37-40,42,51,53,55,60H,22-25H2,1-6H3,(H,50,57)/t26?,32-,33-,34+,37-,38+,39+,40-,42-,47+,48-,49+/m0/s1
SMILES:	CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)CC(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL288847
PubChem CID:	44286531
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

*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
NPO33211	japanese yew	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9873389]

☑ 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	2
Others	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.95	ug.mL-1	PMID[498319]
NPT2	Others	Unspecified		VCR accumulation	=	143.0	n.a.	PMID[498319]
NPT2	Others	Unspecified		VCR accumulation	=	148.0	n.a.	PMID[498319]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.0025	ug.mL-1	PMID[498319]

☑ 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 NPC471606 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	264
0.1-0.2	1091
0.2-0.3	2670
0.3-0.4	7511
0.4-0.5	13381
0.5-0.6	13293
0.6-0.7	4201
0.7-0.8	226
0.8-0.85	12
0.85-0.9	1
0.9-0.95	14
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC208553
1.0	High Similarity	NPC181964
0.9943	High Similarity	NPC191193
0.9943	High Similarity	NPC215892
0.9943	High Similarity	NPC473558
0.9943	High Similarity	NPC321072
0.9943	High Similarity	NPC242662
0.983	High Similarity	NPC473490
0.977	High Similarity	NPC67246
0.977	High Similarity	NPC33372
0.9713	High Similarity	NPC453583
0.9713	High Similarity	NPC475336
0.9713	High Similarity	NPC473300
0.9613	High Similarity	NPC116862
0.96	High Similarity	NPC317882
0.96	High Similarity	NPC324251
0.96	High Similarity	NPC473400
0.96	High Similarity	NPC275170
0.96	High Similarity	NPC471754
0.96	High Similarity	NPC306001
0.96	High Similarity	NPC471629
0.96	High Similarity	NPC206211
0.9598	High Similarity	NPC327699
0.9558	High Similarity	NPC289383
0.9448	High Similarity	NPC472391
0.9432	High Similarity	NPC471623
0.9392	High Similarity	NPC472392
0.9286	High Similarity	NPC472375
0.8913	High Similarity	NPC36607
0.8276	Intermediate Similarity	NPC259144
0.8276	Intermediate Similarity	NPC114357
0.8276	Intermediate Similarity	NPC155329
0.8218	Intermediate Similarity	NPC248265
0.8218	Intermediate Similarity	NPC11588
0.8218	Intermediate Similarity	NPC229545
0.8218	Intermediate Similarity	NPC219419
0.8218	Intermediate Similarity	NPC134685
0.8182	Intermediate Similarity	NPC472393
0.8171	Intermediate Similarity	NPC228204
0.8171	Intermediate Similarity	NPC26033
0.8136	Intermediate Similarity	NPC471102
0.8125	Intermediate Similarity	NPC217091
0.8125	Intermediate Similarity	NPC106895
0.8114	Intermediate Similarity	NPC1173
0.8114	Intermediate Similarity	NPC472030
0.8114	Intermediate Similarity	NPC472022
0.8114	Intermediate Similarity	NPC473414
0.8114	Intermediate Similarity	NPC265395
0.8114	Intermediate Similarity	NPC472005
0.8114	Intermediate Similarity	NPC158333
0.8114	Intermediate Similarity	NPC242262
0.8114	Intermediate Similarity	NPC237549
0.8114	Intermediate Similarity	NPC256142
0.8114	Intermediate Similarity	NPC304876
0.8114	Intermediate Similarity	NPC249471
0.8114	Intermediate Similarity	NPC257213
0.8111	Intermediate Similarity	NPC471493
0.8103	Intermediate Similarity	NPC197037
0.8068	Intermediate Similarity	NPC21410
0.8068	Intermediate Similarity	NPC112523
0.8068	Intermediate Similarity	NPC114410
0.8068	Intermediate Similarity	NPC473670
0.8068	Intermediate Similarity	NPC282239
0.8046	Intermediate Similarity	NPC7095
0.8046	Intermediate Similarity	NPC91730
0.8011	Intermediate Similarity	NPC77719
0.7989	Intermediate Similarity	NPC250046
0.7989	Intermediate Similarity	NPC60509
0.7989	Intermediate Similarity	NPC81698
0.7978	Intermediate Similarity	NPC469771
0.7966	Intermediate Similarity	NPC472549
0.7944	Intermediate Similarity	NPC476077
0.7943	Intermediate Similarity	NPC165260
0.7943	Intermediate Similarity	NPC198455
0.7943	Intermediate Similarity	NPC161239
0.7943	Intermediate Similarity	NPC112216
0.7931	Intermediate Similarity	NPC217918
0.7898	Intermediate Similarity	NPC306799
0.7898	Intermediate Similarity	NPC470153
0.7898	Intermediate Similarity	NPC51602
0.7898	Intermediate Similarity	NPC101043
0.7898	Intermediate Similarity	NPC471103
0.7853	Intermediate Similarity	NPC472548
0.7853	Intermediate Similarity	NPC477905
0.7841	Intermediate Similarity	NPC254558
0.7841	Intermediate Similarity	NPC470245
0.7841	Intermediate Similarity	NPC473214
0.7816	Intermediate Similarity	NPC127857
0.7784	Intermediate Similarity	NPC473215
0.7784	Intermediate Similarity	NPC476975
0.7765	Intermediate Similarity	NPC473632
0.7765	Intermediate Similarity	NPC132599
0.7765	Intermediate Similarity	NPC473611
0.7765	Intermediate Similarity	NPC469730
0.7759	Intermediate Similarity	NPC38696
0.7684	Intermediate Similarity	NPC266265
0.7684	Intermediate Similarity	NPC270590
0.7684	Intermediate Similarity	NPC92293
0.7684	Intermediate Similarity	NPC301556
0.7684	Intermediate Similarity	NPC471101
0.767	Intermediate Similarity	NPC474935
0.7644	Intermediate Similarity	NPC182869
0.7644	Intermediate Similarity	NPC34012
0.7627	Intermediate Similarity	NPC281717
0.7614	Intermediate Similarity	NPC200471
0.7614	Intermediate Similarity	NPC472575
0.7614	Intermediate Similarity	NPC174982
0.7614	Intermediate Similarity	NPC471100
0.7614	Intermediate Similarity	NPC473088
0.7614	Intermediate Similarity	NPC470157
0.7614	Intermediate Similarity	NPC472572
0.7614	Intermediate Similarity	NPC158663
0.7614	Intermediate Similarity	NPC184817
0.7614	Intermediate Similarity	NPC301946
0.7614	Intermediate Similarity	NPC471104
0.7614	Intermediate Similarity	NPC472568
0.7614	Intermediate Similarity	NPC171525
0.7614	Intermediate Similarity	NPC472571
0.7614	Intermediate Similarity	NPC177940
0.7614	Intermediate Similarity	NPC476973
0.7614	Intermediate Similarity	NPC471107
0.7614	Intermediate Similarity	NPC472556
0.7614	Intermediate Similarity	NPC96903
0.7614	Intermediate Similarity	NPC469349
0.7614	Intermediate Similarity	NPC277053
0.7614	Intermediate Similarity	NPC29704
0.7614	Intermediate Similarity	NPC470159
0.7614	Intermediate Similarity	NPC70403
0.7594	Intermediate Similarity	NPC102465
0.7581	Intermediate Similarity	NPC30171
0.7568	Intermediate Similarity	NPC150893
0.7568	Intermediate Similarity	NPC295408
0.7568	Intermediate Similarity	NPC329960
0.7557	Intermediate Similarity	NPC163719
0.7557	Intermediate Similarity	NPC472570
0.7557	Intermediate Similarity	NPC25768
0.7557	Intermediate Similarity	NPC80895
0.7557	Intermediate Similarity	NPC241951
0.7557	Intermediate Similarity	NPC95265
0.7557	Intermediate Similarity	NPC475122
0.7557	Intermediate Similarity	NPC471912
0.7557	Intermediate Similarity	NPC188865
0.7557	Intermediate Similarity	NPC470152
0.7557	Intermediate Similarity	NPC11685
0.7557	Intermediate Similarity	NPC470231
0.7557	Intermediate Similarity	NPC70716
0.7557	Intermediate Similarity	NPC472569
0.7557	Intermediate Similarity	NPC125106
0.7557	Intermediate Similarity	NPC95810
0.7557	Intermediate Similarity	NPC476974
0.7557	Intermediate Similarity	NPC57628
0.7557	Intermediate Similarity	NPC472573
0.7557	Intermediate Similarity	NPC475759
0.7553	Intermediate Similarity	NPC477471
0.7553	Intermediate Similarity	NPC477466
0.7553	Intermediate Similarity	NPC477469
0.7553	Intermediate Similarity	NPC477473
0.7541	Intermediate Similarity	NPC469399
0.7527	Intermediate Similarity	NPC471134
0.7527	Intermediate Similarity	NPC11410
0.75	Intermediate Similarity	NPC96801
0.75	Intermediate Similarity	NPC477894
0.75	Intermediate Similarity	NPC163087
0.75	Intermediate Similarity	NPC150698
0.7488	Intermediate Similarity	NPC314941
0.7486	Intermediate Similarity	NPC213567
0.7486	Intermediate Similarity	NPC469417
0.7473	Intermediate Similarity	NPC251139
0.7473	Intermediate Similarity	NPC66193
0.7472	Intermediate Similarity	NPC94602
0.7471	Intermediate Similarity	NPC472371
0.7471	Intermediate Similarity	NPC472395
0.7463	Intermediate Similarity	NPC315889
0.746	Intermediate Similarity	NPC120667
0.746	Intermediate Similarity	NPC278272
0.7444	Intermediate Similarity	NPC31829
0.7443	Intermediate Similarity	NPC472546
0.7435	Intermediate Similarity	NPC469421
0.7419	Intermediate Similarity	NPC253738
0.7419	Intermediate Similarity	NPC55744
0.7416	Intermediate Similarity	NPC473541
0.7413	Intermediate Similarity	NPC42286
0.7409	Intermediate Similarity	NPC475649
0.7407	Intermediate Similarity	NPC469420
0.7401	Intermediate Similarity	NPC473673
0.7401	Intermediate Similarity	NPC246480
0.7401	Intermediate Similarity	NPC139067
0.7401	Intermediate Similarity	NPC475429
0.7401	Intermediate Similarity	NPC177340
0.7401	Intermediate Similarity	NPC270498
0.7401	Intermediate Similarity	NPC191082
0.7401	Intermediate Similarity	NPC477468
0.7401	Intermediate Similarity	NPC147217
0.7399	Intermediate Similarity	NPC475648
0.7394	Intermediate Similarity	NPC61891
0.7386	Intermediate Similarity	NPC87448
0.7386	Intermediate Similarity	NPC472576
0.7386	Intermediate Similarity	NPC224491
0.7386	Intermediate Similarity	NPC291599
0.7386	Intermediate Similarity	NPC41481

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 NPC471606 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	560
0.2-0.3	1033
0.3-0.4	2341
0.4-0.5	3378
0.5-0.6	1427
0.6-0.7	203
0.7-0.8	14
0.8-0.85	3
0.85-0.9	3
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8485	Approved
0.9831	High Similarity	NPD8486	Clinical (unspecified phase)
0.9432	High Similarity	NPD8361	Approved
0.9432	High Similarity	NPD8435	Approved
0.9432	High Similarity	NPD8360	Approved
0.9101	High Similarity	NPD8424	Clinical (unspecified phase)
0.882	High Similarity	NPD8368	Discontinued
0.8778	High Similarity	NPD8407	Phase 2
0.8444	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.8283	Intermediate Similarity	NPD8462	Phase 1
0.8119	Intermediate Similarity	NPD8404	Phase 2
0.7617	Intermediate Similarity	NPD8150	Discontinued
0.7561	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7874	Approved
0.7488	Intermediate Similarity	NPD8320	Phase 1
0.7488	Intermediate Similarity	NPD8319	Approved
0.7453	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7801	Approved
0.7436	Intermediate Similarity	NPD8434	Phase 2
0.7363	Intermediate Similarity	NPD7699	Phase 2
0.7363	Intermediate Similarity	NPD7700	Phase 2
0.73	Intermediate Similarity	NPD6535	Approved
0.73	Intermediate Similarity	NPD6534	Approved
0.726	Intermediate Similarity	NPD8151	Discontinued
0.715	Intermediate Similarity	NPD7799	Discontinued
0.715	Intermediate Similarity	NPD7871	Phase 2
0.715	Intermediate Similarity	NPD7870	Phase 2
0.7136	Intermediate Similarity	NPD6823	Phase 2
0.7129	Intermediate Similarity	NPD7701	Phase 2
0.7122	Intermediate Similarity	NPD6778	Approved
0.7122	Intermediate Similarity	NPD6779	Approved
0.7122	Intermediate Similarity	NPD6780	Approved
0.7122	Intermediate Similarity	NPD6776	Approved
0.7122	Intermediate Similarity	NPD6777	Approved
0.7122	Intermediate Similarity	NPD6782	Approved
0.7122	Intermediate Similarity	NPD6781	Approved
0.7101	Intermediate Similarity	NPD7696	Phase 3
0.7101	Intermediate Similarity	NPD7698	Approved
0.7101	Intermediate Similarity	NPD7435	Discontinued
0.7101	Intermediate Similarity	NPD7697	Approved
0.7092	Intermediate Similarity	NPD5030	Phase 2
0.7072	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5034	Approved
0.7056	Intermediate Similarity	NPD36	Approved
0.7056	Intermediate Similarity	NPD5026	Approved
0.7056	Intermediate Similarity	NPD5028	Approved
0.7056	Intermediate Similarity	NPD4955	Approved
0.7056	Intermediate Similarity	NPD4954	Approved
0.7035	Intermediate Similarity	NPD5036	Approved
0.7033	Intermediate Similarity	NPD7236	Approved
0.7027	Intermediate Similarity	NPD7239	Suspended
0.7	Intermediate Similarity	NPD5037	Approved
0.7	Intermediate Similarity	NPD5038	Approved
0.6957	Remote Similarity	NPD8468	Phase 2
0.6954	Remote Similarity	NPD3823	Discontinued
0.6946	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7497	Discontinued
0.6816	Remote Similarity	NPD8059	Phase 3
0.6816	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7783	Phase 2
0.6791	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5035	Approved
0.6758	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5029	Approved
0.675	Remote Similarity	NPD5031	Approved
0.675	Remote Similarity	NPD5027	Approved
0.6731	Remote Similarity	NPD7282	Approved
0.6699	Remote Similarity	NPD5968	Phase 3
0.6683	Remote Similarity	NPD6836	Approved
0.6667	Remote Similarity	NPD6212	Phase 3
0.6667	Remote Similarity	NPD6213	Phase 3
0.6667	Remote Similarity	NPD7907	Approved
0.6667	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3819	Phase 2
0.6602	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7057	Phase 3
0.6598	Remote Similarity	NPD7058	Phase 2
0.6588	Remote Similarity	NPD7811	Phase 3
0.6588	Remote Similarity	NPD7810	Phase 3
0.658	Remote Similarity	NPD7972	Discontinued
0.6579	Remote Similarity	NPD8067	Phase 3
0.6557	Remote Similarity	NPD4914	Approved
0.6545	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD8146	Phase 2
0.6533	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6190	Approved
0.652	Remote Similarity	NPD8312	Approved
0.652	Remote Similarity	NPD8313	Approved
0.6518	Remote Similarity	NPD8366	Approved
0.6509	Remote Similarity	NPD8285	Discontinued
0.6509	Remote Similarity	NPD7565	Approved
0.6502	Remote Similarity	NPD4665	Approved
0.6497	Remote Similarity	NPD6746	Phase 2
0.648	Remote Similarity	NPD7075	Discontinued
0.6476	Remote Similarity	NPD8491	Approved
0.6471	Remote Similarity	NPD5032	Approved
0.6471	Remote Similarity	NPD2575	Approved
0.646	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5544	Approved
0.6429	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4111	Phase 1
0.6419	Remote Similarity	NPD4387	Approved
0.6419	Remote Similarity	NPD4386	Approved
0.6418	Remote Similarity	NPD7473	Discontinued
0.641	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7460	Discontinued
0.6402	Remote Similarity	NPD3300	Phase 2
0.64	Remote Similarity	NPD5242	Approved
0.6386	Remote Similarity	NPD7177	Discontinued
0.6386	Remote Similarity	NPD3751	Discontinued
0.6383	Remote Similarity	NPD8166	Discontinued
0.6378	Remote Similarity	NPD5402	Approved
0.6374	Remote Similarity	NPD7715	Approved
0.6374	Remote Similarity	NPD7714	Approved
0.6374	Remote Similarity	NPD7713	Phase 3
0.6372	Remote Similarity	NPD2494	Approved
0.6372	Remote Similarity	NPD3452	Approved
0.6372	Remote Similarity	NPD2493	Approved
0.6372	Remote Similarity	NPD3450	Approved
0.6368	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD6166	Phase 2
0.6359	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD4582	Approved
0.6359	Remote Similarity	NPD4583	Approved
0.6359	Remote Similarity	NPD6801	Discontinued
0.6359	Remote Similarity	NPD7029	Discontinued
0.6355	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5844	Phase 1
0.6351	Remote Similarity	NPD4466	Phase 1
0.6348	Remote Similarity	NPD7654	Discontinued
0.634	Remote Similarity	NPD6599	Discontinued
0.6338	Remote Similarity	NPD2973	Approved
0.6338	Remote Similarity	NPD2975	Approved
0.6338	Remote Similarity	NPD2974	Approved
0.6326	Remote Similarity	NPD4580	Approved
0.6324	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD7930	Approved
0.6313	Remote Similarity	NPD4004	Approved
0.6313	Remote Similarity	NPD4002	Approved
0.6311	Remote Similarity	NPD7962	Phase 2
0.6308	Remote Similarity	NPD6385	Approved
0.6308	Remote Similarity	NPD6386	Approved
0.6301	Remote Similarity	NPD7584	Approved
0.6301	Remote Similarity	NPD7583	Approved
0.6296	Remote Similarity	NPD4628	Phase 3
0.6296	Remote Similarity	NPD3400	Discontinued
0.6291	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7458	Discontinued
0.6287	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD7961	Discontinued
0.628	Remote Similarity	NPD7546	Discontinued
0.6279	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7585	Approved
0.6271	Remote Similarity	NPD6287	Discontinued
0.627	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD7315	Approved
0.6269	Remote Similarity	NPD3787	Discontinued
0.6269	Remote Similarity	NPD6232	Discontinued
0.6267	Remote Similarity	NPD3057	Approved
0.6264	Remote Similarity	NPD7008	Discontinued
0.6264	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7038	Approved
0.6262	Remote Similarity	NPD7039	Approved
0.6262	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD6502	Phase 2
0.6256	Remote Similarity	NPD7999	Approved
0.6256	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD4380	Phase 2
0.6244	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7819	Suspended
0.624	Remote Similarity	NPD8367	Approved
0.6238	Remote Similarity	NPD7693	Approved
0.6233	Remote Similarity	NPD4974	Approved
0.6233	Remote Similarity	NPD4975	Approved
0.6232	Remote Similarity	NPD7808	Phase 3
0.6232	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD7048	Phase 3
0.6224	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD8127	Discontinued
0.6214	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD3817	Phase 2
0.6212	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6894	Phase 1
0.6207	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD3455	Phase 2
0.6204	Remote Similarity	NPD8492	Approved
0.6204	Remote Similarity	NPD5608	Approved
0.6204	Remote Similarity	NPD6874	Approved
0.6204	Remote Similarity	NPD5609	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