NPASS Compound

Structure

CID223356 OpenBabel06191716022D 42 47 0 0 1 0 0 0 0 0999 V2000 6.8734 1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9484 -2.5947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7184 -3.0712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9754 1.0971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4719 -1.7001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5884 -2.3464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5199 0.8500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7589 0.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3515 1.4623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5905 1.4312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1831 2.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4221 2.0436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0147 2.6870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2538 2.6559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5396 0.0138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4306 2.4705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1959 -2.4779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1368 1.0194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5554 -1.3127 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9984 -2.8281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3986 0.2710 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6040 -0.3856 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3650 1.8981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.8522 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2065 0.6169 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3170 -1.3127 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3129 2.0773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7985 1.7130 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7616 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.2907 1.4356 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7616 -1.8522 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5554 -0.5395 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9026 3.1679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1205 -3.5798 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5502 2.7197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4237 2.9122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4830 1.6741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2863 -2.5579 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9518 1.5183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3170 -0.5395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1187 -0.9260 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 7 1 0 0 0 0 2 17 2 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 20 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 2 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 14 29 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 33 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 19 32 1 1 0 0 0 20 34 2 0 0 0 0 20 38 1 0 0 0 0 21 30 1 6 0 0 0 21 32 1 0 0 0 0 22 25 1 0 0 0 0 22 26 1 0 0 0 0 22 32 1 1 0 0 0 23 30 1 0 0 0 0 23 35 2 0 0 0 0 24 31 1 6 0 0 0 24 38 1 0 0 0 0 25 28 1 1 0 0 0 25 39 1 0 0 0 0 26 31 1 1 0 0 0 26 40 1 0 0 0 0 27 28 1 6 0 0 0 27 30 1 0 0 0 0 27 36 1 0 0 0 0 28 16 1 6 0 0 0 28 39 1 0 0 0 0 29 40 1 0 0 0 0 29 41 1 0 0 0 0 29 42 1 0 0 0 0 30 37 1 6 0 0 0 31 17 1 1 0 0 0 31 41 1 0 0 0 0 32 42 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.11
Volume:	369.43
LogP:	4.23
LogD:	3.412
LogS:	-4.16
# Rotatable Bonds:	1
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.781
Synthetic Accessibility Score:	3.637
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.936
MDCK Permeability:	2.208476871601306e-05
Pgp-inhibitor:	0.19
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	100.8690185546875%
Volume Distribution (VD):	0.427
Pgp-substrate:	0.5470432043075562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.866
CYP1A2-substrate:	0.428
CYP2C19-inhibitor:	0.89
CYP2C19-substrate:	0.268
CYP2C9-inhibitor:	0.897
CYP2C9-substrate:	0.861
CYP2D6-inhibitor:	0.934
CYP2D6-substrate:	0.623
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.313

ADMET: Excretion

Clearance (CL):	12.154
Half-life (T1/2):	0.117

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.292
Drug-inuced Liver Injury (DILI):	0.831
AMES Toxicity:	0.102
Rat Oral Acute Toxicity:	0.424
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.846
Carcinogencity:	0.909
Eye Corrosion:	0.003
Eye Irritation:	0.284
Respiratory Toxicity:	0.466

Download Data

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

Natural Product: NPC223356

Natural Product ID:	NPC223356
*Common Name:**	Isoyuanhuadine
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NHELFTYSELEEFD-COIZZEIWSA-N
Standard InCHI:	InChI=1S/C32H42O10/c1-7-8-9-10-11-12-13-14-29-40-26-22-25-28(16-33,39-25)27(36)30(37)21(15-18(4)23(30)35)32(22,42-29)19(5)24(38-20(6)34)31(26,41-29)17(2)3/h11-15,19,21-22,24-27,33,36-37H,2,7-10,16H2,1,3-6H3/b12-11-,14-13+/t19-,21-,22+,24-,25+,26-,27-,28+,29?,30-,31+,32+/m1/s1
SMILES:	CCCCC/C=CC=CC12O[C@H]3[C@](O1)(C(=C)C)[C@@H]([C@H]([C@@]1(O2)[C@H]3[C@@H]2O[C@@]2([C@H]([C@]2([C@H]1C=C(C2=O)C)O)O)CO)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2376818
PubChem CID:	73345818
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	10

Activity Type	# Activity
Cell Line	9
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	=	17540.0	nM	PMID[479193]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	17430.0	nM	PMID[479193]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	17720.0	nM	PMID[479193]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	14890.0	nM	PMID[479193]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	24120.0	nM	PMID[479193]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	32310.0	nM	PMID[479193]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	30000.0	nM	PMID[479193]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	23450.0	nM	PMID[479193]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	640.0	nM	PMID[479193]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21520.0	nM	PMID[479193]

☑ 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 NPC223356 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	291
0.1-0.2	1473
0.2-0.3	4147
0.3-0.4	7197
0.4-0.5	12281
0.5-0.6	10201
0.6-0.7	5496
0.7-0.8	1451
0.8-0.85	103
0.85-0.9	14
0.9-0.95	10
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471137
1.0	High Similarity	NPC475500
1.0	High Similarity	NPC182266
1.0	High Similarity	NPC473548
1.0	High Similarity	NPC100017
1.0	High Similarity	NPC471136
1.0	High Similarity	NPC475154
0.9839	High Similarity	NPC68282
0.9836	High Similarity	NPC474508
0.9836	High Similarity	NPC180902
0.9836	High Similarity	NPC473485
0.9836	High Similarity	NPC475139
0.9754	High Similarity	NPC477189
0.9754	High Similarity	NPC475606
0.9754	High Similarity	NPC475314
0.9754	High Similarity	NPC251564
0.9672	High Similarity	NPC162495
0.9508	High Similarity	NPC475273
0.9508	High Similarity	NPC168849
0.9426	High Similarity	NPC217901
0.9426	High Similarity	NPC471939
0.935	High Similarity	NPC471940
0.928	High Similarity	NPC473838
0.928	High Similarity	NPC475389
0.9262	High Similarity	NPC473802
0.9187	High Similarity	NPC473919
0.9187	High Similarity	NPC473709
0.912	High Similarity	NPC476091
0.912	High Similarity	NPC476078
0.8968	High Similarity	NPC236999
0.8672	High Similarity	NPC270109
0.8583	High Similarity	NPC145238
0.8571	High Similarity	NPC257017
0.8571	High Similarity	NPC162009
0.856	High Similarity	NPC142882
0.8516	High Similarity	NPC222307
0.8504	High Similarity	NPC472399
0.8425	Intermediate Similarity	NPC19464
0.8413	Intermediate Similarity	NPC317635
0.8413	Intermediate Similarity	NPC329008
0.8346	Intermediate Similarity	NPC52839
0.8346	Intermediate Similarity	NPC472401
0.8333	Intermediate Similarity	NPC470186
0.8308	Intermediate Similarity	NPC298841
0.8299	Intermediate Similarity	NPC49297
0.8268	Intermediate Similarity	NPC185876
0.8268	Intermediate Similarity	NPC471126
0.8268	Intermediate Similarity	NPC475885
0.8268	Intermediate Similarity	NPC472759
0.8268	Intermediate Similarity	NPC157252
0.8268	Intermediate Similarity	NPC145182
0.8268	Intermediate Similarity	NPC471128
0.8268	Intermediate Similarity	NPC329080
0.8268	Intermediate Similarity	NPC19336
0.8254	Intermediate Similarity	NPC124676
0.8254	Intermediate Similarity	NPC146280
0.8231	Intermediate Similarity	NPC181924
0.8209	Intermediate Similarity	NPC471234
0.8203	Intermediate Similarity	NPC102822
0.8203	Intermediate Similarity	NPC477046
0.8195	Intermediate Similarity	NPC471855
0.8189	Intermediate Similarity	NPC156745
0.8189	Intermediate Similarity	NPC180640
0.8189	Intermediate Similarity	NPC471108
0.8189	Intermediate Similarity	NPC5989
0.8189	Intermediate Similarity	NPC236918
0.8189	Intermediate Similarity	NPC5991
0.8189	Intermediate Similarity	NPC22628
0.8189	Intermediate Similarity	NPC255081
0.8189	Intermediate Similarity	NPC275696
0.8168	Intermediate Similarity	NPC42399
0.8154	Intermediate Similarity	NPC470922
0.8133	Intermediate Similarity	NPC477188
0.8133	Intermediate Similarity	NPC43304
0.8133	Intermediate Similarity	NPC477190
0.8133	Intermediate Similarity	NPC275477
0.8125	Intermediate Similarity	NPC472004
0.8125	Intermediate Similarity	NPC143755
0.812	Intermediate Similarity	NPC476852
0.811	Intermediate Similarity	NPC471125
0.811	Intermediate Similarity	NPC284707
0.811	Intermediate Similarity	NPC472758
0.811	Intermediate Similarity	NPC472397
0.811	Intermediate Similarity	NPC171905
0.811	Intermediate Similarity	NPC472760
0.8106	Intermediate Similarity	NPC473620
0.8095	Intermediate Similarity	NPC477509
0.8092	Intermediate Similarity	NPC473635
0.8092	Intermediate Similarity	NPC225049
0.8092	Intermediate Similarity	NPC181999
0.8088	Intermediate Similarity	NPC243014
0.808	Intermediate Similarity	NPC477126
0.8079	Intermediate Similarity	NPC322420
0.8077	Intermediate Similarity	NPC469352
0.8071	Intermediate Similarity	NPC471172
0.806	Intermediate Similarity	NPC470185
0.8047	Intermediate Similarity	NPC476107
0.8047	Intermediate Similarity	NPC469488
0.8047	Intermediate Similarity	NPC472667
0.8047	Intermediate Similarity	NPC476529
0.8047	Intermediate Similarity	NPC475775
0.8045	Intermediate Similarity	NPC475371
0.8045	Intermediate Similarity	NPC476851
0.8045	Intermediate Similarity	NPC471407
0.8045	Intermediate Similarity	NPC470851
0.8045	Intermediate Similarity	NPC231529
0.8031	Intermediate Similarity	NPC153651
0.8031	Intermediate Similarity	NPC98249
0.8031	Intermediate Similarity	NPC10721
0.8031	Intermediate Similarity	NPC156252
0.8031	Intermediate Similarity	NPC53396
0.803	Intermediate Similarity	NPC287423
0.803	Intermediate Similarity	NPC470780
0.8029	Intermediate Similarity	NPC596
0.8027	Intermediate Similarity	NPC146310
0.8016	Intermediate Similarity	NPC73314
0.8015	Intermediate Similarity	NPC24651
0.8014	Intermediate Similarity	NPC48813
0.8014	Intermediate Similarity	NPC194854
0.8	Intermediate Similarity	NPC168879
0.7985	Intermediate Similarity	NPC476862
0.7985	Intermediate Similarity	NPC476855
0.7985	Intermediate Similarity	NPC471170
0.7985	Intermediate Similarity	NPC476863
0.7984	Intermediate Similarity	NPC475003
0.7984	Intermediate Similarity	NPC112038
0.7984	Intermediate Similarity	NPC48692
0.7984	Intermediate Similarity	NPC109607
0.7984	Intermediate Similarity	NPC107338
0.7974	Intermediate Similarity	NPC61891
0.797	Intermediate Similarity	NPC470850
0.797	Intermediate Similarity	NPC476859
0.7969	Intermediate Similarity	NPC188667
0.7969	Intermediate Similarity	NPC204552
0.7967	Intermediate Similarity	NPC29827
0.7958	Intermediate Similarity	NPC475462
0.7958	Intermediate Similarity	NPC16729
0.7956	Intermediate Similarity	NPC190065
0.7956	Intermediate Similarity	NPC141215
0.7956	Intermediate Similarity	NPC471089
0.7955	Intermediate Similarity	NPC293112
0.7953	Intermediate Similarity	NPC471127
0.7953	Intermediate Similarity	NPC154363
0.7953	Intermediate Similarity	NPC234858
0.7941	Intermediate Similarity	NPC242486
0.7941	Intermediate Similarity	NPC15215
0.7939	Intermediate Similarity	NPC91693
0.7939	Intermediate Similarity	NPC471392
0.7939	Intermediate Similarity	NPC265557
0.7939	Intermediate Similarity	NPC11895
0.7939	Intermediate Similarity	NPC18945
0.7939	Intermediate Similarity	NPC105926
0.7939	Intermediate Similarity	NPC67251
0.7937	Intermediate Similarity	NPC469454
0.7937	Intermediate Similarity	NPC469463
0.7937	Intermediate Similarity	NPC469496
0.7937	Intermediate Similarity	NPC474937
0.7929	Intermediate Similarity	NPC48414
0.7929	Intermediate Similarity	NPC5153
0.7926	Intermediate Similarity	NPC33378
0.7926	Intermediate Similarity	NPC254614
0.7926	Intermediate Similarity	NPC254146
0.7926	Intermediate Similarity	NPC231240
0.7926	Intermediate Similarity	NPC102316
0.7926	Intermediate Similarity	NPC472769
0.7926	Intermediate Similarity	NPC6274
0.7926	Intermediate Similarity	NPC100390
0.7923	Intermediate Similarity	NPC470779
0.7923	Intermediate Similarity	NPC204731
0.7923	Intermediate Similarity	NPC310511
0.791	Intermediate Similarity	NPC175186
0.791	Intermediate Similarity	NPC476966
0.791	Intermediate Similarity	NPC104382
0.791	Intermediate Similarity	NPC470880
0.791	Intermediate Similarity	NPC476854
0.791	Intermediate Similarity	NPC473593
0.7907	Intermediate Similarity	NPC9674
0.7907	Intermediate Similarity	NPC19028
0.7899	Intermediate Similarity	NPC140045
0.7899	Intermediate Similarity	NPC295885
0.7895	Intermediate Similarity	NPC470882
0.7895	Intermediate Similarity	NPC473253
0.7895	Intermediate Similarity	NPC476008
0.7891	Intermediate Similarity	NPC97908
0.7891	Intermediate Similarity	NPC469684
0.7891	Intermediate Similarity	NPC122033
0.7891	Intermediate Similarity	NPC287343
0.7891	Intermediate Similarity	NPC474654
0.7891	Intermediate Similarity	NPC470854
0.7891	Intermediate Similarity	NPC23046
0.7886	Intermediate Similarity	NPC474716
0.7883	Intermediate Similarity	NPC262813
0.7879	Intermediate Similarity	NPC75856
0.7879	Intermediate Similarity	NPC476729
0.7879	Intermediate Similarity	NPC86346
0.7879	Intermediate Similarity	NPC469379
0.7879	Intermediate Similarity	NPC172154
0.7879	Intermediate Similarity	NPC81736
0.7879	Intermediate Similarity	NPC8369
0.7874	Intermediate Similarity	NPC474872

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 NPC223356 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	1579
0.2-0.3	3627
0.3-0.4	2428
0.4-0.5	752
0.5-0.6	339
0.6-0.7	155
0.7-0.8	27
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
0.7742	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD8517	Approved
0.7652	Intermediate Similarity	NPD8515	Approved
0.7652	Intermediate Similarity	NPD8513	Phase 3
0.7652	Intermediate Similarity	NPD8516	Approved
0.7647	Intermediate Similarity	NPD7319	Approved
0.7612	Intermediate Similarity	NPD7492	Approved
0.7576	Intermediate Similarity	NPD6054	Approved
0.7574	Intermediate Similarity	NPD7736	Approved
0.7556	Intermediate Similarity	NPD6616	Approved
0.754	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7078	Approved
0.7463	Intermediate Similarity	NPD6370	Approved
0.7426	Intermediate Similarity	NPD7507	Approved
0.7388	Intermediate Similarity	NPD6016	Approved
0.7388	Intermediate Similarity	NPD6015	Approved
0.7372	Intermediate Similarity	NPD8293	Discontinued
0.7372	Intermediate Similarity	NPD8074	Phase 3
0.7348	Intermediate Similarity	NPD7115	Discovery
0.7333	Intermediate Similarity	NPD5988	Approved
0.7313	Intermediate Similarity	NPD6319	Approved
0.7313	Intermediate Similarity	NPD6059	Approved
0.7287	Intermediate Similarity	NPD6371	Approved
0.7279	Intermediate Similarity	NPD8328	Phase 3
0.7239	Intermediate Similarity	NPD7516	Approved
0.72	Intermediate Similarity	NPD5344	Discontinued
0.7176	Intermediate Similarity	NPD8297	Approved
0.7176	Intermediate Similarity	NPD6882	Approved
0.7164	Intermediate Similarity	NPD7328	Approved
0.7164	Intermediate Similarity	NPD7327	Approved
0.7153	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6686	Approved
0.712	Intermediate Similarity	NPD6648	Approved
0.7099	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6009	Approved
0.7077	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7503	Approved
0.7007	Intermediate Similarity	NPD8335	Approved
0.7007	Intermediate Similarity	NPD8380	Approved
0.7007	Intermediate Similarity	NPD8378	Approved
0.7007	Intermediate Similarity	NPD8033	Approved
0.7007	Intermediate Similarity	NPD8379	Approved
0.7007	Intermediate Similarity	NPD8296	Approved
0.7007	Intermediate Similarity	NPD6921	Approved
0.6992	Remote Similarity	NPD4632	Approved
0.697	Remote Similarity	NPD6650	Approved
0.697	Remote Similarity	NPD6649	Approved
0.6963	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD8294	Approved
0.6934	Remote Similarity	NPD8377	Approved
0.6906	Remote Similarity	NPD7829	Approved
0.6906	Remote Similarity	NPD7830	Approved
0.6905	Remote Similarity	NPD4225	Approved
0.6885	Remote Similarity	NPD6698	Approved
0.6885	Remote Similarity	NPD7838	Discovery
0.6885	Remote Similarity	NPD46	Approved
0.687	Remote Similarity	NPD6899	Approved
0.687	Remote Similarity	NPD6881	Approved
0.6846	Remote Similarity	NPD6008	Approved
0.6842	Remote Similarity	NPD8130	Phase 1
0.6831	Remote Similarity	NPD6033	Approved
0.6829	Remote Similarity	NPD7983	Approved
0.6818	Remote Similarity	NPD6373	Approved
0.6818	Remote Similarity	NPD6372	Approved
0.6794	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5697	Approved
0.6791	Remote Similarity	NPD6053	Discontinued
0.6786	Remote Similarity	NPD7604	Phase 2
0.6784	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7290	Approved
0.6767	Remote Similarity	NPD4634	Approved
0.6767	Remote Similarity	NPD7102	Approved
0.6767	Remote Similarity	NPD6883	Approved
0.6742	Remote Similarity	NPD7320	Approved
0.6741	Remote Similarity	NPD8133	Approved
0.6718	Remote Similarity	NPD5739	Approved
0.6718	Remote Similarity	NPD6675	Approved
0.6718	Remote Similarity	NPD7128	Approved
0.6718	Remote Similarity	NPD6402	Approved
0.6716	Remote Similarity	NPD6617	Approved
0.6716	Remote Similarity	NPD6869	Approved
0.6716	Remote Similarity	NPD6847	Approved
0.6692	Remote Similarity	NPD6013	Approved
0.6692	Remote Similarity	NPD6014	Approved
0.6692	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6012	Approved
0.669	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD7642	Approved
0.6667	Remote Similarity	NPD1695	Approved
0.6644	Remote Similarity	NPD8338	Approved
0.6643	Remote Similarity	NPD5983	Phase 2
0.664	Remote Similarity	NPD5779	Approved
0.664	Remote Similarity	NPD5778	Approved
0.6617	Remote Similarity	NPD6011	Approved
0.6607	Remote Similarity	NPD7799	Discontinued
0.6587	Remote Similarity	NPD5282	Discontinued
0.6573	Remote Similarity	NPD8451	Approved
0.6573	Remote Similarity	NPD6336	Discontinued
0.6541	Remote Similarity	NPD5701	Approved
0.6541	Remote Similarity	NPD6412	Phase 2
0.6532	Remote Similarity	NPD8407	Phase 2
0.6531	Remote Similarity	NPD6845	Suspended
0.6528	Remote Similarity	NPD8448	Approved
0.6512	Remote Similarity	NPD7638	Approved
0.6489	Remote Similarity	NPD5211	Phase 2
0.6484	Remote Similarity	NPD7839	Suspended
0.6462	Remote Similarity	NPD5285	Approved
0.6462	Remote Similarity	NPD4696	Approved
0.6462	Remote Similarity	NPD5286	Approved
0.6462	Remote Similarity	NPD7639	Approved
0.6462	Remote Similarity	NPD7640	Approved
0.6453	Remote Similarity	NPD8368	Discontinued
0.6412	Remote Similarity	NPD1700	Approved
0.6408	Remote Similarity	NPD8444	Approved
0.6408	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6101	Approved
0.64	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5956	Approved
0.6395	Remote Similarity	NPD8391	Approved
0.6395	Remote Similarity	NPD8390	Approved
0.6395	Remote Similarity	NPD8392	Approved
0.6391	Remote Similarity	NPD5141	Approved
0.6389	Remote Similarity	NPD8341	Approved
0.6389	Remote Similarity	NPD8342	Approved
0.6389	Remote Similarity	NPD8340	Approved
0.6389	Remote Similarity	NPD8299	Approved
0.6383	Remote Similarity	NPD7100	Approved
0.6383	Remote Similarity	NPD7101	Approved
0.6364	Remote Similarity	NPD4633	Approved
0.6364	Remote Similarity	NPD5226	Approved
0.6364	Remote Similarity	NPD5224	Approved
0.6364	Remote Similarity	NPD5225	Approved
0.635	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD8273	Phase 1
0.6333	Remote Similarity	NPD8415	Approved
0.6316	Remote Similarity	NPD5174	Approved
0.6316	Remote Similarity	NPD5175	Approved
0.6312	Remote Similarity	NPD6335	Approved
0.6312	Remote Similarity	NPD7641	Discontinued
0.6308	Remote Similarity	NPD4755	Approved
0.6299	Remote Similarity	NPD6411	Approved
0.6291	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD5223	Approved
0.6286	Remote Similarity	NPD6274	Approved
0.6259	Remote Similarity	NPD8336	Approved
0.6259	Remote Similarity	NPD8337	Approved
0.625	Remote Similarity	NPD8080	Discontinued
0.625	Remote Similarity	NPD4730	Approved
0.625	Remote Similarity	NPD4729	Approved
0.6241	Remote Similarity	NPD6317	Approved
0.6212	Remote Similarity	NPD4700	Approved
0.621	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD6314	Approved
0.6197	Remote Similarity	NPD6313	Approved
0.6183	Remote Similarity	NPD6084	Phase 2
0.6183	Remote Similarity	NPD6083	Phase 2
0.618	Remote Similarity	NPD8434	Phase 2
0.6172	Remote Similarity	NPD7637	Suspended
0.6159	Remote Similarity	NPD5248	Approved
0.6159	Remote Similarity	NPD5247	Approved
0.6159	Remote Similarity	NPD5249	Phase 3
0.6159	Remote Similarity	NPD5250	Approved
0.6159	Remote Similarity	NPD5251	Approved
0.6111	Remote Similarity	NPD8360	Approved
0.6111	Remote Similarity	NPD8435	Approved
0.6111	Remote Similarity	NPD8361	Approved
0.6107	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD5221	Approved
0.6107	Remote Similarity	NPD5222	Approved
0.6103	Remote Similarity	NPD4767	Approved
0.6103	Remote Similarity	NPD4768	Approved
0.6096	Remote Similarity	NPD6067	Discontinued
0.6094	Remote Similarity	NPD5785	Approved
0.6092	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.608	Remote Similarity	NPD1694	Approved
0.6069	Remote Similarity	NPD8267	Approved
0.6069	Remote Similarity	NPD8266	Approved
0.6069	Remote Similarity	NPD6908	Approved
0.6069	Remote Similarity	NPD6909	Approved
0.6069	Remote Similarity	NPD8269	Approved
0.6069	Remote Similarity	NPD8268	Approved
0.6069	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7902	Approved
0.6061	Remote Similarity	NPD5173	Approved
0.6056	Remote Similarity	NPD6868	Approved
0.6047	Remote Similarity	NPD6079	Approved
0.6044	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD5695	Phase 3
0.6031	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD7236	Approved
0.6015	Remote Similarity	NPD5696	Approved
0.6014	Remote Similarity	NPD5128	Approved
0.6	Remote Similarity	NPD5215	Approved
0.6	Remote Similarity	NPD5216	Approved
0.6	Remote Similarity	NPD6333	Approved
0.6	Remote Similarity	NPD7632	Discontinued

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