NPASS Compound

Structure

NPC471139 OpenBabel07101719402D 47 52 0 0 1 0 0 0 0 0999 V2000 -3.9488 -10.3220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2175 -1.9385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9872 -3.1577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5434 3.4418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5330 1.1631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4878 -9.4797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0279 -8.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5669 -7.7494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1069 -6.8615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6459 -6.0192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1860 -5.1312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0609 0.8836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1949 1.3836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0609 -0.1164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7250 -4.2889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3289 0.8836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1949 -0.6164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2650 -3.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9035 1.7786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8690 -0.5361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3451 -1.6251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2504 -2.1930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6472 2.4472 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2105 0.2165 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3289 -0.1164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3095 0.8648 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8040 -2.5587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0930 -0.9241 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5128 1.9465 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0341 -1.2622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4345 -1.6767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0054 0.2556 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8852 -0.7372 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5465 -1.4827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3041 0.9685 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7705 0.0225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4628 -0.6164 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.8030 -2.6043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4267 2.3525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1379 -2.2568 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9519 0.5781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8841 -0.7828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7689 0.0831 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3441 -1.6708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2695 -1.3626 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0716 -1.0914 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 22 2 0 0 0 0 3 22 1 0 0 0 0 5 24 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 2 0 0 0 0 11 15 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 16 1 0 0 0 0 14 17 2 0 0 0 0 15 18 2 0 0 0 0 16 25 2 0 0 0 0 17 25 1 0 0 0 0 18 27 1 0 0 0 0 19 23 1 0 0 0 0 19 26 1 0 0 0 0 20 24 1 0 0 0 0 20 34 1 0 0 0 0 21 33 1 0 0 0 0 21 44 1 0 0 0 0 23 4 1 1 0 0 0 23 29 1 0 0 0 0 24 36 1 6 0 0 0 25 37 1 0 0 0 0 26 35 1 1 0 0 0 26 36 1 0 0 0 0 27 38 2 0 0 0 0 27 44 1 0 0 0 0 28 30 1 0 0 0 0 28 31 1 0 0 0 0 28 36 1 6 0 0 0 29 35 1 1 0 0 0 29 39 1 0 0 0 0 30 33 1 6 0 0 0 30 40 1 0 0 0 0 31 34 1 1 0 0 0 31 45 1 0 0 0 0 32 33 1 1 0 0 0 32 35 1 0 0 0 0 32 41 1 0 0 0 0 33 42 1 1 0 0 0 34 22 1 6 0 0 0 34 46 1 0 0 0 0 35 43 1 1 0 0 0 36 47 1 6 0 0 0 37 45 1 0 0 0 0 37 46 1 0 0 0 0 37 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	654.34
Volume:	666.616
LogP:	4.844
LogD:	3.546
LogS:	-4.044
# Rotatable Bonds:	11
TPSA:	155.14
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.083
Synthetic Accessibility Score:	6.723
Fsp3:	0.649
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.862
MDCK Permeability:	3.685928459162824e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.951
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.544
30% Bioavailability (F30%):	0.624

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.242
Plasma Protein Binding (PPB):	97.26608276367188%
Volume Distribution (VD):	1.563
Pgp-substrate:	0.9670222401618958%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.858
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.777
CYP2C9-inhibitor:	0.531
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.633
CYP3A4-substrate:	0.263

ADMET: Excretion

Clearance (CL):	1.979
Half-life (T1/2):	0.675

ADMET: Toxicity

hERG Blockers:	0.447
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.802
AMES Toxicity:	0.421
Rat Oral Acute Toxicity:	0.915
Maximum Recommended Daily Dose:	0.997
Skin Sensitization:	0.913
Carcinogencity:	0.318
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC471139

Natural Product ID:	NPC471139
*Common Name:**	XGZZGUNAJRVNQJ-UINOGJBISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XGZZGUNAJRVNQJ-UINOGJBISA-N
Standard InCHI:	InChI=1S/C37H50O10/c1-6-7-8-9-10-11-15-18-27(38)44-21-33(42)30(40)28-31-34(22(2)3)20-24(5)36(28,26-19-23(4)29(39)35(26,43)32(33)41)47-37(45-31,46-34)25-16-13-12-14-17-25/h10-18,23-24,26,28-32,39-43H,2,6-9,19-21H2,1,3-5H3/b11-10+,18-15+/t23-,24+,26+,28-,29-,30-,31+,32+,33+,34+,35+,36-,37?/m0/s1
SMILES:	CCCCCC=CC=CC(=O)OCC1(C(C2C3C4(CC(C2(C5CC(C(C5(C1O)O)O)C)OC(O3)(O4)C6=CC=CC=C6)C)C(=C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2376824
PubChem CID:	72188654
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
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	flower	n.a.	PMID[21916433]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[23558238]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228307]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31150241]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31860304]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223193]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9756	Daphne genkwa	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	12

Activity Type	# Activity
Cell Line	11
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	24190.0	nM	PMID[489400]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	23840.0	nM	PMID[489400]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	20500.0	nM	PMID[489400]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	29940.0	nM	PMID[489400]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	22290.0	nM	PMID[489400]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	27430.0	nM	PMID[489400]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	22660.0	nM	PMID[489400]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[489400]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	26170.0	nM	PMID[489400]
NPT319	Cell Line	B16	Mus musculus	IC50	>	30000.0	nM	PMID[489401]
NPT319	Cell Line	B16	Mus musculus	IC50	=	570.0	nM	PMID[489401]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	25410.0	nM	PMID[489400]

☑ 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 NPC471139 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	322
0.1-0.2	1177
0.2-0.3	2678
0.3-0.4	5701
0.4-0.5	10324
0.5-0.6	16424
0.6-0.7	5154
0.7-0.8	715
0.8-0.85	158
0.85-0.9	27
0.9-0.95	16
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9441	High Similarity	NPC471135
0.9437	High Similarity	NPC62792
0.931	High Similarity	NPC475638
0.931	High Similarity	NPC475548
0.931	High Similarity	NPC290683
0.9301	High Similarity	NPC478123
0.9301	High Similarity	NPC298072
0.9247	High Similarity	NPC322048
0.9247	High Similarity	NPC318447
0.9178	High Similarity	NPC323001
0.9178	High Similarity	NPC326235
0.9122	High Similarity	NPC323356
0.9122	High Similarity	NPC471138
0.9122	High Similarity	NPC326328
0.9122	High Similarity	NPC309991
0.9071	High Similarity	NPC325078
0.8926	High Similarity	NPC319404
0.8889	High Similarity	NPC312393
0.8874	High Similarity	NPC478124
0.8836	High Similarity	NPC476173
0.8699	High Similarity	NPC327031
0.8693	High Similarity	NPC478125
0.8675	High Similarity	NPC49297
0.8667	High Similarity	NPC154675
0.8609	High Similarity	NPC181924
0.859	High Similarity	NPC40138
0.8514	High Similarity	NPC76103
0.8514	High Similarity	NPC474564
0.8506	High Similarity	NPC477188
0.8506	High Similarity	NPC477190
0.8506	High Similarity	NPC43304
0.8506	High Similarity	NPC275477
0.8503	High Similarity	NPC240115
0.8462	Intermediate Similarity	NPC324769
0.8462	Intermediate Similarity	NPC325732
0.8456	Intermediate Similarity	NPC476092
0.8456	Intermediate Similarity	NPC475218
0.8456	Intermediate Similarity	NPC475447
0.8456	Intermediate Similarity	NPC70236
0.8452	Intermediate Similarity	NPC66193
0.8411	Intermediate Similarity	NPC146310
0.8406	Intermediate Similarity	NPC476971
0.8406	Intermediate Similarity	NPC476972
0.84	Intermediate Similarity	NPC96308
0.8397	Intermediate Similarity	NPC471134
0.8378	Intermediate Similarity	NPC478263
0.8367	Intermediate Similarity	NPC34943
0.8345	Intermediate Similarity	NPC58061
0.8344	Intermediate Similarity	NPC61891
0.8333	Intermediate Similarity	NPC475561
0.8333	Intermediate Similarity	NPC475933
0.8333	Intermediate Similarity	NPC475417
0.8333	Intermediate Similarity	NPC470158
0.8333	Intermediate Similarity	NPC476970
0.8312	Intermediate Similarity	NPC476784
0.8311	Intermediate Similarity	NPC478264
0.8289	Intermediate Similarity	NPC472658
0.8289	Intermediate Similarity	NPC472657
0.8288	Intermediate Similarity	NPC16912
0.8288	Intermediate Similarity	NPC291599
0.8288	Intermediate Similarity	NPC87448
0.8288	Intermediate Similarity	NPC41481
0.8288	Intermediate Similarity	NPC118080
0.8288	Intermediate Similarity	NPC27377
0.8288	Intermediate Similarity	NPC472576
0.8288	Intermediate Similarity	NPC97947
0.8278	Intermediate Similarity	NPC469415
0.8261	Intermediate Similarity	NPC284022
0.8255	Intermediate Similarity	NPC20255
0.8239	Intermediate Similarity	NPC476976
0.8235	Intermediate Similarity	NPC34066
0.8235	Intermediate Similarity	NPC469422
0.8231	Intermediate Similarity	NPC192658
0.8228	Intermediate Similarity	NPC473468
0.8228	Intermediate Similarity	NPC477491
0.8228	Intermediate Similarity	NPC473557
0.8228	Intermediate Similarity	NPC475567
0.8219	Intermediate Similarity	NPC275592
0.8219	Intermediate Similarity	NPC97667
0.8219	Intermediate Similarity	NPC100913
0.8219	Intermediate Similarity	NPC90614
0.8219	Intermediate Similarity	NPC171207
0.8217	Intermediate Similarity	NPC322420
0.8212	Intermediate Similarity	NPC303429
0.8212	Intermediate Similarity	NPC222102
0.82	Intermediate Similarity	NPC473760
0.8188	Intermediate Similarity	NPC472568
0.8188	Intermediate Similarity	NPC470157
0.8188	Intermediate Similarity	NPC174982
0.8188	Intermediate Similarity	NPC92867
0.8188	Intermediate Similarity	NPC184817
0.8188	Intermediate Similarity	NPC158663
0.8188	Intermediate Similarity	NPC171525
0.8188	Intermediate Similarity	NPC311825
0.8188	Intermediate Similarity	NPC200471
0.8188	Intermediate Similarity	NPC476973
0.8188	Intermediate Similarity	NPC472571
0.8188	Intermediate Similarity	NPC473088
0.8188	Intermediate Similarity	NPC125882
0.8188	Intermediate Similarity	NPC469349
0.8188	Intermediate Similarity	NPC29704
0.8188	Intermediate Similarity	NPC471104
0.8188	Intermediate Similarity	NPC177940
0.8188	Intermediate Similarity	NPC472575
0.8188	Intermediate Similarity	NPC96903
0.8188	Intermediate Similarity	NPC472572
0.8188	Intermediate Similarity	NPC70403
0.8188	Intermediate Similarity	NPC470159
0.8176	Intermediate Similarity	NPC131966
0.8176	Intermediate Similarity	NPC475175
0.8176	Intermediate Similarity	NPC475531
0.8176	Intermediate Similarity	NPC475198
0.8176	Intermediate Similarity	NPC191387
0.8169	Intermediate Similarity	NPC476977
0.8141	Intermediate Similarity	NPC477623
0.8133	Intermediate Similarity	NPC48599
0.8133	Intermediate Similarity	NPC473602
0.8133	Intermediate Similarity	NPC209592
0.8121	Intermediate Similarity	NPC95265
0.8121	Intermediate Similarity	NPC25768
0.8121	Intermediate Similarity	NPC163719
0.8121	Intermediate Similarity	NPC188865
0.8121	Intermediate Similarity	NPC57628
0.8121	Intermediate Similarity	NPC475122
0.8121	Intermediate Similarity	NPC11685
0.8121	Intermediate Similarity	NPC475759
0.8121	Intermediate Similarity	NPC241951
0.8121	Intermediate Similarity	NPC470152
0.8121	Intermediate Similarity	NPC472573
0.8121	Intermediate Similarity	NPC472569
0.8121	Intermediate Similarity	NPC70716
0.8121	Intermediate Similarity	NPC125106
0.8121	Intermediate Similarity	NPC472570
0.8121	Intermediate Similarity	NPC95810
0.8121	Intermediate Similarity	NPC476974
0.8117	Intermediate Similarity	NPC471176
0.8117	Intermediate Similarity	NPC469456
0.8117	Intermediate Similarity	NPC469398
0.8116	Intermediate Similarity	NPC473870
0.8116	Intermediate Similarity	NPC473871
0.8108	Intermediate Similarity	NPC34012
0.8101	Intermediate Similarity	NPC269668
0.8095	Intermediate Similarity	NPC472547
0.8095	Intermediate Similarity	NPC87934
0.8095	Intermediate Similarity	NPC162613
0.8092	Intermediate Similarity	NPC469448
0.8085	Intermediate Similarity	NPC230331
0.8075	Intermediate Similarity	NPC477488
0.8065	Intermediate Similarity	NPC70344
0.8054	Intermediate Similarity	NPC163087
0.8052	Intermediate Similarity	NPC133430
0.8052	Intermediate Similarity	NPC469477
0.8043	Intermediate Similarity	NPC70973
0.8043	Intermediate Similarity	NPC473889
0.8041	Intermediate Similarity	NPC266374
0.8027	Intermediate Similarity	NPC9905
0.8026	Intermediate Similarity	NPC476975
0.8026	Intermediate Similarity	NPC471101
0.8026	Intermediate Similarity	NPC301556
0.8026	Intermediate Similarity	NPC92293
0.8026	Intermediate Similarity	NPC270590
0.8026	Intermediate Similarity	NPC266265
0.8013	Intermediate Similarity	NPC474935
0.8	Intermediate Similarity	NPC473083
0.8	Intermediate Similarity	NPC471758
0.8	Intermediate Similarity	NPC251139
0.7987	Intermediate Similarity	NPC473755
0.7987	Intermediate Similarity	NPC475513
0.7974	Intermediate Similarity	NPC470245
0.7974	Intermediate Similarity	NPC473214
0.7974	Intermediate Similarity	NPC31829
0.7973	Intermediate Similarity	NPC473440
0.7971	Intermediate Similarity	NPC37641
0.7971	Intermediate Similarity	NPC229600
0.7971	Intermediate Similarity	NPC311175
0.7962	Intermediate Similarity	NPC469399
0.7961	Intermediate Similarity	NPC320734
0.7961	Intermediate Similarity	NPC281717
0.7959	Intermediate Similarity	NPC39549
0.7947	Intermediate Similarity	NPC251062
0.7947	Intermediate Similarity	NPC184464
0.7947	Intermediate Similarity	NPC472556
0.7945	Intermediate Similarity	NPC66761
0.7945	Intermediate Similarity	NPC17877
0.7945	Intermediate Similarity	NPC472577
0.7945	Intermediate Similarity	NPC200154
0.7945	Intermediate Similarity	NPC195647
0.7945	Intermediate Similarity	NPC291638
0.7943	Intermediate Similarity	NPC473111
0.7943	Intermediate Similarity	NPC45821
0.7943	Intermediate Similarity	NPC473110
0.7933	Intermediate Similarity	NPC91703
0.7925	Intermediate Similarity	NPC165234
0.7925	Intermediate Similarity	NPC55744
0.7925	Intermediate Similarity	NPC475536
0.7922	Intermediate Similarity	NPC470153
0.7914	Intermediate Similarity	NPC286809
0.7908	Intermediate Similarity	NPC473215
0.7905	Intermediate Similarity	NPC473301
0.7905	Intermediate Similarity	NPC53361

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 NPC471139 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	748
0.2-0.3	1661
0.3-0.4	3257
0.4-0.5	2182
0.5-0.6	909
0.6-0.7	133
0.7-0.8	10
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
0.7805	Intermediate Similarity	NPD7799	Discontinued
0.777	Intermediate Similarity	NPD5125	Phase 3
0.777	Intermediate Similarity	NPD5126	Approved
0.7544	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7741	Discontinued
0.7372	Intermediate Similarity	NPD7236	Approved
0.7337	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7266	Discontinued
0.7273	Intermediate Similarity	NPD5763	Approved
0.7273	Intermediate Similarity	NPD5762	Approved
0.725	Intermediate Similarity	NPD7239	Suspended
0.7184	Intermediate Similarity	NPD8407	Phase 2
0.7183	Intermediate Similarity	NPD7516	Approved
0.7162	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7328	Approved
0.7113	Intermediate Similarity	NPD7327	Approved
0.711	Intermediate Similarity	NPD8368	Discontinued
0.711	Intermediate Similarity	NPD7685	Pre-registration
0.7089	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4967	Phase 2
0.7048	Intermediate Similarity	NPD4965	Approved
0.7048	Intermediate Similarity	NPD4966	Approved
0.702	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD8127	Discontinued
0.6982	Remote Similarity	NPD7199	Phase 2
0.6977	Remote Similarity	NPD7228	Approved
0.697	Remote Similarity	NPD37	Approved
0.6966	Remote Similarity	NPD8379	Approved
0.6966	Remote Similarity	NPD8033	Approved
0.6966	Remote Similarity	NPD7503	Approved
0.6966	Remote Similarity	NPD8380	Approved
0.6966	Remote Similarity	NPD8296	Approved
0.6966	Remote Similarity	NPD8378	Approved
0.6966	Remote Similarity	NPD8335	Approved
0.6964	Remote Similarity	NPD6234	Discontinued
0.6923	Remote Similarity	NPD4198	Discontinued
0.6897	Remote Similarity	NPD8377	Approved
0.6897	Remote Similarity	NPD8294	Approved
0.6879	Remote Similarity	NPD969	Suspended
0.6845	Remote Similarity	NPD7057	Phase 3
0.6845	Remote Similarity	NPD7058	Phase 2
0.6839	Remote Similarity	NPD5735	Approved
0.6818	Remote Similarity	NPD7240	Approved
0.6816	Remote Similarity	NPD8434	Phase 2
0.6802	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4140	Approved
0.6763	Remote Similarity	NPD6685	Approved
0.6755	Remote Similarity	NPD3094	Phase 2
0.675	Remote Similarity	NPD6674	Discontinued
0.6748	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7028	Phase 2
0.674	Remote Similarity	NPD8361	Approved
0.674	Remote Similarity	NPD8435	Approved
0.674	Remote Similarity	NPD8360	Approved
0.673	Remote Similarity	NPD6002	Phase 3
0.673	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6005	Phase 3
0.673	Remote Similarity	NPD6004	Phase 3
0.6727	Remote Similarity	NPD1653	Approved
0.6707	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD7497	Discontinued
0.6667	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6190	Approved
0.6646	Remote Similarity	NPD7097	Phase 1
0.663	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD8455	Phase 2
0.6605	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6663	Approved
0.66	Remote Similarity	NPD3092	Approved
0.6582	Remote Similarity	NPD6653	Approved
0.6556	Remote Similarity	NPD7507	Approved
0.6556	Remote Similarity	NPD8312	Approved
0.6556	Remote Similarity	NPD8313	Approved
0.6547	Remote Similarity	NPD5765	Approved
0.6538	Remote Similarity	NPD8150	Discontinued
0.6536	Remote Similarity	NPD6765	Approved
0.6536	Remote Similarity	NPD6764	Approved
0.6536	Remote Similarity	NPD7319	Approved
0.6536	Remote Similarity	NPD6559	Discontinued
0.6533	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5760	Phase 2
0.6529	Remote Similarity	NPD5761	Phase 2
0.6528	Remote Similarity	NPD6912	Phase 3
0.6524	Remote Similarity	NPD5058	Phase 3
0.6519	Remote Similarity	NPD5124	Phase 1
0.6519	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD2629	Approved
0.6506	Remote Similarity	NPD6273	Approved
0.6503	Remote Similarity	NPD8166	Discontinued
0.6485	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD6353	Approved
0.6461	Remote Similarity	NPD5844	Phase 1
0.6456	Remote Similarity	NPD3620	Phase 2
0.6456	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2861	Phase 2
0.6438	Remote Similarity	NPD5886	Approved
0.6438	Remote Similarity	NPD41	Approved
0.6433	Remote Similarity	NPD7819	Suspended
0.6429	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6355	Discontinued
0.6402	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD4628	Phase 3
0.6396	Remote Similarity	NPD8462	Phase 1
0.6393	Remote Similarity	NPD6784	Approved
0.6393	Remote Similarity	NPD6785	Approved
0.6392	Remote Similarity	NPD7961	Discontinued
0.6391	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6085	Phase 2
0.6387	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.637	Remote Similarity	NPD6858	Approved
0.637	Remote Similarity	NPD7094	Approved
0.6358	Remote Similarity	NPD3095	Discontinued
0.6352	Remote Similarity	NPD4060	Phase 1
0.6349	Remote Similarity	NPD8485	Approved
0.6345	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD1652	Phase 2
0.6341	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3091	Approved
0.6329	Remote Similarity	NPD3764	Approved
0.6329	Remote Similarity	NPD7985	Registered
0.6327	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7075	Discontinued
0.6322	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7680	Approved
0.6316	Remote Similarity	NPD7700	Phase 2
0.6316	Remote Similarity	NPD7699	Phase 2
0.6313	Remote Similarity	NPD3751	Discontinued
0.6313	Remote Similarity	NPD3818	Discontinued
0.6312	Remote Similarity	NPD6647	Phase 2
0.6309	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD5327	Phase 3
0.6289	Remote Similarity	NPD8320	Phase 1
0.6289	Remote Similarity	NPD8319	Approved
0.6286	Remote Similarity	NPD5344	Discontinued
0.6283	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD4624	Approved
0.6278	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD1091	Approved
0.6275	Remote Similarity	NPD7492	Approved
0.6275	Remote Similarity	NPD3705	Approved
0.6272	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD3787	Discontinued
0.6266	Remote Similarity	NPD3027	Phase 3
0.6264	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD7137	Phase 2
0.6258	Remote Similarity	NPD7736	Approved
0.6257	Remote Similarity	NPD4380	Phase 2
0.6256	Remote Similarity	NPD7999	Approved
0.625	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1613	Approved
0.625	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD7074	Phase 3
0.6243	Remote Similarity	NPD6534	Approved
0.6243	Remote Similarity	NPD6535	Approved
0.6237	Remote Similarity	NPD7435	Discontinued
0.6235	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD6616	Approved
0.6226	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD6054	Approved
0.6218	Remote Similarity	NPD6362	Approved
0.6214	Remote Similarity	NPD6648	Approved
0.62	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD7458	Discontinued
0.6196	Remote Similarity	NPD7033	Discontinued
0.6194	Remote Similarity	NPD7078	Approved
0.6194	Remote Similarity	NPD7876	Discontinued
0.6188	Remote Similarity	NPD7054	Approved
0.6188	Remote Similarity	NPD4404	Approved
0.6184	Remote Similarity	NPD5691	Approved
0.6182	Remote Similarity	NPD2424	Discontinued
0.6174	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD7930	Approved
0.6167	Remote Similarity	NPD7473	Discontinued
0.6164	Remote Similarity	NPD7008	Discontinued
0.6164	Remote Similarity	NPD7095	Approved
0.6162	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD5494	Approved
0.6154	Remote Similarity	NPD8651	Approved
0.6154	Remote Similarity	NPD7472	Approved
0.615	Remote Similarity	NPD6841	Approved
0.615	Remote Similarity	NPD6843	Phase 3
0.615	Remote Similarity	NPD6842	Approved
0.6144	Remote Similarity	NPD4626	Approved
0.6144	Remote Similarity	NPD6370	Approved
0.6141	Remote Similarity	NPD7808	Phase 3
0.6141	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD6686	Approved
0.6131	Remote Similarity	NPD7874	Approved
0.6131	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.612	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD5402	Approved
0.6108	Remote Similarity	NPD4109	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