NPASS Compound

Structure

CID186746 OpenBabel06191715562D 44 50 0 0 1 0 0 0 0 0999 V2000 1.6889 -1.5874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5181 0.0377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7717 -5.7173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8302 -2.8096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0982 0.0206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9332 1.7967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2812 0.4923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0982 -0.9228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9925 1.8673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3425 0.9468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4642 0.0206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2812 -1.3945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4610 1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8111 0.1673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1927 -4.1390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9677 -4.5080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9382 0.0986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1344 -0.8242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0801 -5.0756 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.0131 -2.3379 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4642 -0.9228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8704 0.2378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3367 -3.7424 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6209 -2.3379 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1545 -5.2580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0131 -1.3945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4990 -2.6825 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6209 -1.3945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6472 -1.3945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2457 -4.3635 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7771 -3.5840 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3049 -4.4340 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1961 -0.9228 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1961 -2.8096 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8632 -4.8049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2421 -6.1140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6472 -2.3379 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7174 -5.1805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1850 -4.0942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3219 -0.7632 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 1.8302 -0.9228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7446 -2.8801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4188 -2.8925 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 22 2 0 0 0 0 14 22 1 0 0 0 0 15 19 1 0 0 0 0 15 23 1 0 0 0 0 16 35 1 0 0 0 0 17 40 1 0 0 0 0 17 41 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 20 34 1 1 0 0 0 21 29 1 0 0 0 0 22 43 1 0 0 0 0 23 32 1 6 0 0 0 23 34 1 0 0 0 0 24 27 1 0 0 0 0 24 28 1 0 0 0 0 24 34 1 1 0 0 0 25 32 1 0 0 0 0 25 36 2 0 0 0 0 26 33 1 6 0 0 0 26 42 1 0 0 0 0 27 31 1 1 0 0 0 27 44 1 0 0 0 0 28 33 1 1 0 0 0 28 40 1 0 0 0 0 29 37 2 0 0 0 0 29 42 1 0 0 0 0 30 31 1 6 0 0 0 30 32 1 0 0 0 0 30 38 1 0 0 0 0 31 16 1 6 0 0 0 31 44 1 0 0 0 0 32 39 1 6 0 0 0 33 18 1 6 0 0 0 33 41 1 0 0 0 0 34 43 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	606.25
Volume:	600.899
LogP:	3.366
LogD:	3.061
LogS:	-4.062
# Rotatable Bonds:	7
TPSA:	144.28
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.255
Synthetic Accessibility Score:	5.59
Fsp3:	0.529
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:	-5.268
MDCK Permeability:	6.961997132748365e-05
Pgp-inhibitor:	0.243
Pgp-substrate:	0.727
Human Intestinal Absorption (HIA):	0.057
20% Bioavailability (F20%):	0.793
30% Bioavailability (F30%):	0.593

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.305
Plasma Protein Binding (PPB):	94.17652130126953%
Volume Distribution (VD):	1.748
Pgp-substrate:	3.1454224586486816%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.658
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.185
CYP2C9-inhibitor:	0.17
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.113
CYP3A4-inhibitor:	0.246
CYP3A4-substrate:	0.345

ADMET: Excretion

Clearance (CL):	9.459
Half-life (T1/2):	0.763

ADMET: Toxicity

hERG Blockers:	0.636
Human Hepatotoxicity (H-HT):	0.997
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.372
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.182
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC186746

Natural Product ID:	NPC186746
*Common Name:**	Yuanhuatin
IUPAC Name:	n.a.
Synonyms:	Yuanhuatin
Standard InCHIKey:	YIDJXVBIMGGUNX-DSFRSVAISA-N
Standard InCHI:	InChI=1S/C34H38O10/c1-18(2)33-26(42-29(37)21-11-7-5-8-12-21)20(4)34(43-22-13-9-6-10-14-22)23-15-19(3)25(36)32(23,39)30(38)31(16-35)27(44-31)24(34)28(33)40-17-41-33/h5-14,19-20,23-24,26-28,30,35,38-39H,1,15-17H2,2-4H3/t19?,20-,23-,24+,26-,27+,28-,30-,31+,32-,33+,34+/m1/s1
SMILES:	OC[C@]12O[C@H]1[C@H]1[C@H]3OCO[C@@]3(C(=C)C)[C@@H]([C@H]([C@@]1([C@H]1[C@@]([C@@H]2O)(O)C(=O)C(C1)C)Oc1ccccc1)C)OC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1096217
PubChem CID:	46886775
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
NPO2035	Daphne aurantiaca	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192236]
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]
NPO2035	Daphne aurantiaca	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	60.0	nM	PMID[482305]

☑ 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 NPC186746 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	409
0.1-0.2	1587
0.2-0.3	3105
0.3-0.4	6583
0.4-0.5	10803
0.5-0.6	7964
0.6-0.7	8389
0.7-0.8	3726
0.8-0.85	123
0.85-0.9	6
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC254588
0.9053	High Similarity	NPC40138
0.8824	High Similarity	NPC61891
0.8764	High Similarity	NPC105395
0.8757	High Similarity	NPC477188
0.8757	High Similarity	NPC43304
0.8757	High Similarity	NPC477190
0.8713	High Similarity	NPC325732
0.8713	High Similarity	NPC324769
0.8706	High Similarity	NPC66193
0.8659	High Similarity	NPC242068
0.8659	High Similarity	NPC247563
0.8655	High Similarity	NPC471134
0.8647	High Similarity	NPC275477
0.858	High Similarity	NPC49297
0.8571	High Similarity	NPC154675
0.8547	High Similarity	NPC108191
0.8547	High Similarity	NPC93685
0.8539	High Similarity	NPC11062
0.8531	High Similarity	NPC195972
0.8529	High Similarity	NPC471138
0.8529	High Similarity	NPC323356
0.8529	High Similarity	NPC326328
0.8529	High Similarity	NPC309991
0.8521	High Similarity	NPC181924
0.8488	Intermediate Similarity	NPC322420
0.8466	Intermediate Similarity	NPC475237
0.8466	Intermediate Similarity	NPC475641
0.8462	Intermediate Similarity	NPC290683
0.8462	Intermediate Similarity	NPC475548
0.8462	Intermediate Similarity	NPC475638
0.8436	Intermediate Similarity	NPC272656
0.8412	Intermediate Similarity	NPC322048
0.8412	Intermediate Similarity	NPC318447
0.8402	Intermediate Similarity	NPC251139
0.8391	Intermediate Similarity	NPC259943
0.8389	Intermediate Similarity	NPC470938
0.8371	Intermediate Similarity	NPC471632
0.8371	Intermediate Similarity	NPC148185
0.8361	Intermediate Similarity	NPC299855
0.8361	Intermediate Similarity	NPC96194
0.8353	Intermediate Similarity	NPC323001
0.8353	Intermediate Similarity	NPC326235
0.8343	Intermediate Similarity	NPC471135
0.8343	Intermediate Similarity	NPC146310
0.8343	Intermediate Similarity	NPC161151
0.8333	Intermediate Similarity	NPC316457
0.8333	Intermediate Similarity	NPC472669
0.8324	Intermediate Similarity	NPC167340
0.8324	Intermediate Similarity	NPC55744
0.8315	Intermediate Similarity	NPC189704
0.8305	Intermediate Similarity	NPC118086
0.8305	Intermediate Similarity	NPC470995
0.8305	Intermediate Similarity	NPC472659
0.8297	Intermediate Similarity	NPC208069
0.8286	Intermediate Similarity	NPC477491
0.8276	Intermediate Similarity	NPC472668
0.8276	Intermediate Similarity	NPC188649
0.827	Intermediate Similarity	NPC476067
0.827	Intermediate Similarity	NPC475121
0.8268	Intermediate Similarity	NPC149502
0.8268	Intermediate Similarity	NPC271755
0.8268	Intermediate Similarity	NPC254071
0.8268	Intermediate Similarity	NPC222665
0.8258	Intermediate Similarity	NPC294512
0.8249	Intermediate Similarity	NPC242334
0.8249	Intermediate Similarity	NPC472673
0.8249	Intermediate Similarity	NPC296558
0.8249	Intermediate Similarity	NPC469419
0.8245	Intermediate Similarity	NPC314687
0.8239	Intermediate Similarity	NPC121995
0.8239	Intermediate Similarity	NPC327694
0.8239	Intermediate Similarity	NPC120012
0.8229	Intermediate Similarity	NPC288602
0.8229	Intermediate Similarity	NPC88841
0.8226	Intermediate Similarity	NPC314672
0.8226	Intermediate Similarity	NPC71385
0.8226	Intermediate Similarity	NPC230670
0.8218	Intermediate Similarity	NPC478124
0.8212	Intermediate Similarity	NPC469848
0.8208	Intermediate Similarity	NPC88007
0.8208	Intermediate Similarity	NPC194499
0.8208	Intermediate Similarity	NPC195954
0.8202	Intermediate Similarity	NPC472650
0.8192	Intermediate Similarity	NPC318472
0.8182	Intermediate Similarity	NPC326278
0.8182	Intermediate Similarity	NPC261184
0.8182	Intermediate Similarity	NPC112708
0.8177	Intermediate Similarity	NPC107739
0.8171	Intermediate Similarity	NPC68848
0.8171	Intermediate Similarity	NPC130489
0.8171	Intermediate Similarity	NPC471166
0.8171	Intermediate Similarity	NPC79571
0.8171	Intermediate Similarity	NPC208676
0.8171	Intermediate Similarity	NPC18986
0.8171	Intermediate Similarity	NPC478125
0.8171	Intermediate Similarity	NPC471167
0.8167	Intermediate Similarity	NPC94763
0.8156	Intermediate Similarity	NPC159232
0.8156	Intermediate Similarity	NPC21956
0.8152	Intermediate Similarity	NPC473776
0.8152	Intermediate Similarity	NPC473205
0.815	Intermediate Similarity	NPC159692
0.8146	Intermediate Similarity	NPC271235
0.8146	Intermediate Similarity	NPC477488
0.8146	Intermediate Similarity	NPC469396
0.8146	Intermediate Similarity	NPC469458
0.8146	Intermediate Similarity	NPC88176
0.8146	Intermediate Similarity	NPC472652
0.8146	Intermediate Similarity	NPC160651
0.8146	Intermediate Similarity	NPC149002
0.8142	Intermediate Similarity	NPC236089
0.814	Intermediate Similarity	NPC106895
0.8138	Intermediate Similarity	NPC475299
0.8138	Intermediate Similarity	NPC473711
0.8132	Intermediate Similarity	NPC475613
0.8132	Intermediate Similarity	NPC23593
0.8125	Intermediate Similarity	NPC476035
0.8125	Intermediate Similarity	NPC285567
0.8125	Intermediate Similarity	NPC14499
0.8125	Intermediate Similarity	NPC475039
0.8125	Intermediate Similarity	NPC477627
0.8125	Intermediate Similarity	NPC283209
0.8122	Intermediate Similarity	NPC470438
0.8122	Intermediate Similarity	NPC469633
0.8122	Intermediate Similarity	NPC316539
0.8122	Intermediate Similarity	NPC98776
0.8122	Intermediate Similarity	NPC476311
0.8122	Intermediate Similarity	NPC477881
0.8122	Intermediate Similarity	NPC176413
0.8122	Intermediate Similarity	NPC56953
0.8118	Intermediate Similarity	NPC471103
0.8118	Intermediate Similarity	NPC51602
0.8114	Intermediate Similarity	NPC8389
0.8114	Intermediate Similarity	NPC209473
0.8114	Intermediate Similarity	NPC470789
0.8108	Intermediate Similarity	NPC106700
0.8101	Intermediate Similarity	NPC103633
0.8101	Intermediate Similarity	NPC473094
0.8101	Intermediate Similarity	NPC302392
0.8101	Intermediate Similarity	NPC82602
0.8098	Intermediate Similarity	NPC102367
0.8098	Intermediate Similarity	NPC188217
0.8092	Intermediate Similarity	NPC478232
0.809	Intermediate Similarity	NPC472651
0.809	Intermediate Similarity	NPC310572
0.809	Intermediate Similarity	NPC102465
0.809	Intermediate Similarity	NPC472774
0.809	Intermediate Similarity	NPC270312
0.809	Intermediate Similarity	NPC472282
0.809	Intermediate Similarity	NPC472775
0.8087	Intermediate Similarity	NPC476199
0.8087	Intermediate Similarity	NPC476210
0.8087	Intermediate Similarity	NPC29587
0.8081	Intermediate Similarity	NPC282239
0.8079	Intermediate Similarity	NPC126984
0.8079	Intermediate Similarity	NPC27541
0.8079	Intermediate Similarity	NPC206815
0.8079	Intermediate Similarity	NPC62692
0.8077	Intermediate Similarity	NPC469438
0.8077	Intermediate Similarity	NPC472158
0.8077	Intermediate Similarity	NPC186800
0.8077	Intermediate Similarity	NPC470667
0.8068	Intermediate Similarity	NPC73422
0.8068	Intermediate Similarity	NPC5741
0.8068	Intermediate Similarity	NPC310399
0.8068	Intermediate Similarity	NPC474936
0.8066	Intermediate Similarity	NPC469576
0.8066	Intermediate Similarity	NPC236004
0.8066	Intermediate Similarity	NPC471437
0.8066	Intermediate Similarity	NPC477617
0.8056	Intermediate Similarity	NPC285227
0.8056	Intermediate Similarity	NPC102810
0.8056	Intermediate Similarity	NPC473202
0.8056	Intermediate Similarity	NPC473096
0.8056	Intermediate Similarity	NPC473095
0.8054	Intermediate Similarity	NPC478001
0.8054	Intermediate Similarity	NPC475656
0.8054	Intermediate Similarity	NPC475148
0.8054	Intermediate Similarity	NPC473883
0.8046	Intermediate Similarity	NPC319404
0.8046	Intermediate Similarity	NPC469399
0.8045	Intermediate Similarity	NPC469459
0.8045	Intermediate Similarity	NPC476277
0.8045	Intermediate Similarity	NPC472150
0.8045	Intermediate Similarity	NPC472766
0.8045	Intermediate Similarity	NPC282551
0.8045	Intermediate Similarity	NPC113093
0.8045	Intermediate Similarity	NPC471397
0.8045	Intermediate Similarity	NPC472765
0.8043	Intermediate Similarity	NPC473729
0.8035	Intermediate Similarity	NPC11410
0.8034	Intermediate Similarity	NPC471286
0.8034	Intermediate Similarity	NPC86800
0.8034	Intermediate Similarity	NPC277618
0.8034	Intermediate Similarity	NPC307781
0.8034	Intermediate Similarity	NPC91288
0.8034	Intermediate Similarity	NPC97574
0.8034	Intermediate Similarity	NPC472141
0.8034	Intermediate Similarity	NPC109990

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 NPC186746 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	877
0.2-0.3	1877
0.3-0.4	2740
0.4-0.5	2030
0.5-0.6	944
0.6-0.7	266
0.7-0.8	73
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
0.8547	High Similarity	NPD8055	Clinical (unspecified phase)
0.8297	Intermediate Similarity	NPD8434	Phase 2
0.8122	Intermediate Similarity	NPD7685	Pre-registration
0.8118	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7799	Discontinued
0.7933	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD7199	Phase 2
0.7838	Intermediate Similarity	NPD8313	Approved
0.7838	Intermediate Similarity	NPD8312	Approved
0.7802	Intermediate Similarity	NPD3751	Discontinued
0.7802	Intermediate Similarity	NPD3818	Discontinued
0.7784	Intermediate Similarity	NPD5760	Phase 2
0.7784	Intermediate Similarity	NPD5761	Phase 2
0.7784	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3787	Discontinued
0.776	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD7075	Discontinued
0.7697	Intermediate Similarity	NPD4966	Approved
0.7697	Intermediate Similarity	NPD4965	Approved
0.7697	Intermediate Similarity	NPD4967	Phase 2
0.7688	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7819	Suspended
0.7654	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6559	Discontinued
0.7634	Intermediate Similarity	NPD6765	Approved
0.7634	Intermediate Similarity	NPD6764	Approved
0.7627	Intermediate Similarity	NPD6801	Discontinued
0.7627	Intermediate Similarity	NPD37	Approved
0.7614	Intermediate Similarity	NPD7435	Discontinued
0.7611	Intermediate Similarity	NPD6234	Discontinued
0.7594	Intermediate Similarity	NPD7808	Phase 3
0.7542	Intermediate Similarity	NPD5402	Approved
0.7542	Intermediate Similarity	NPD3817	Phase 2
0.754	Intermediate Similarity	NPD7251	Discontinued
0.7539	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD8127	Discontinued
0.7527	Intermediate Similarity	NPD7074	Phase 3
0.7526	Intermediate Similarity	NPD8150	Discontinued
0.7514	Intermediate Similarity	NPD7228	Approved
0.7514	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7487	Intermediate Similarity	NPD6797	Phase 2
0.7487	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6273	Approved
0.7475	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7874	Approved
0.7474	Intermediate Similarity	NPD6785	Approved
0.7474	Intermediate Similarity	NPD6784	Approved
0.7473	Intermediate Similarity	NPD5844	Phase 1
0.7473	Intermediate Similarity	NPD7054	Approved
0.7473	Intermediate Similarity	NPD5494	Approved
0.7471	Intermediate Similarity	NPD6799	Approved
0.7462	Intermediate Similarity	NPD6781	Approved
0.7462	Intermediate Similarity	NPD6777	Approved
0.7462	Intermediate Similarity	NPD6776	Approved
0.7462	Intermediate Similarity	NPD6779	Approved
0.7462	Intermediate Similarity	NPD6780	Approved
0.7462	Intermediate Similarity	NPD6778	Approved
0.7462	Intermediate Similarity	NPD6782	Approved
0.7459	Intermediate Similarity	NPD7473	Discontinued
0.7443	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD7697	Approved
0.7437	Intermediate Similarity	NPD7696	Phase 3
0.7437	Intermediate Similarity	NPD7698	Approved
0.7433	Intermediate Similarity	NPD7472	Approved
0.7427	Intermediate Similarity	NPD8404	Phase 2
0.7427	Intermediate Similarity	NPD5762	Approved
0.7427	Intermediate Similarity	NPD5763	Approved
0.7421	Intermediate Similarity	NPD8407	Phase 2
0.7414	Intermediate Similarity	NPD7236	Approved
0.7405	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6166	Phase 2
0.7403	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3882	Suspended
0.74	Intermediate Similarity	NPD7870	Phase 2
0.74	Intermediate Similarity	NPD7871	Phase 2
0.7389	Intermediate Similarity	NPD8455	Phase 2
0.7376	Intermediate Similarity	NPD7701	Phase 2
0.7371	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7458	Discontinued
0.736	Intermediate Similarity	NPD3226	Approved
0.7354	Intermediate Similarity	NPD8368	Discontinued
0.7354	Intermediate Similarity	NPD7240	Approved
0.7353	Intermediate Similarity	NPD7801	Approved
0.7348	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5403	Approved
0.733	Intermediate Similarity	NPD5401	Approved
0.7322	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD4380	Phase 2
0.7313	Intermediate Similarity	NPD8319	Approved
0.7313	Intermediate Similarity	NPD8320	Phase 1
0.7303	Intermediate Similarity	NPD7239	Suspended
0.7297	Intermediate Similarity	NPD6232	Discontinued
0.7293	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7411	Suspended
0.7273	Intermediate Similarity	NPD7700	Phase 2
0.7273	Intermediate Similarity	NPD7699	Phase 2
0.7264	Intermediate Similarity	NPD7497	Discontinued
0.7257	Intermediate Similarity	NPD6190	Approved
0.7246	Intermediate Similarity	NPD7930	Approved
0.7241	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD1934	Approved
0.7235	Intermediate Similarity	NPD6355	Discontinued
0.7232	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7028	Phase 2
0.7209	Intermediate Similarity	NPD2799	Discontinued
0.7208	Intermediate Similarity	NPD6534	Approved
0.7208	Intermediate Similarity	NPD6535	Approved
0.7198	Intermediate Similarity	NPD2801	Approved
0.7192	Intermediate Similarity	NPD7999	Approved
0.7184	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7783	Phase 2
0.7179	Intermediate Similarity	NPD8435	Approved
0.7179	Intermediate Similarity	NPD8361	Approved
0.7179	Intermediate Similarity	NPD8360	Approved
0.7174	Intermediate Similarity	NPD3749	Approved
0.7171	Intermediate Similarity	NPD8151	Discontinued
0.7135	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6823	Phase 2
0.7128	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2346	Discontinued
0.7126	Intermediate Similarity	NPD6004	Phase 3
0.7126	Intermediate Similarity	NPD6002	Phase 3
0.7126	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6005	Phase 3
0.7126	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7768	Phase 2
0.711	Intermediate Similarity	NPD7033	Discontinued
0.7076	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2796	Approved
0.7059	Intermediate Similarity	NPD6959	Discontinued
0.7043	Intermediate Similarity	NPD919	Approved
0.7039	Intermediate Similarity	NPD2533	Approved
0.7039	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2532	Approved
0.7039	Intermediate Similarity	NPD2534	Approved
0.7024	Intermediate Similarity	NPD5647	Approved
0.7018	Intermediate Similarity	NPD6233	Phase 2
0.7016	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1512	Approved
0.699	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD1549	Phase 2
0.6984	Remote Similarity	NPD3926	Phase 2
0.6978	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1247	Approved
0.6965	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD920	Approved
0.6959	Remote Similarity	NPD6798	Discontinued
0.6959	Remote Similarity	NPD2313	Discontinued
0.6954	Remote Similarity	NPD7097	Phase 1
0.6946	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7057	Phase 3
0.6935	Remote Similarity	NPD7058	Phase 2
0.6932	Remote Similarity	NPD1471	Phase 3
0.6932	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7229	Phase 3
0.6919	Remote Similarity	NPD1465	Phase 2
0.691	Remote Similarity	NPD3750	Approved
0.6906	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6653	Approved
0.6897	Remote Similarity	NPD8285	Discontinued
0.6889	Remote Similarity	NPD1511	Approved
0.6879	Remote Similarity	NPD4140	Approved
0.6875	Remote Similarity	NPD2935	Discontinued
0.6875	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3764	Approved
0.686	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7680	Approved
0.6842	Remote Similarity	NPD6832	Phase 2
0.6839	Remote Similarity	NPD5735	Approved
0.6839	Remote Similarity	NPD1933	Approved
0.6824	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2798	Approved
0.6821	Remote Similarity	NPD8032	Phase 2
0.6818	Remote Similarity	NPD3748	Approved
0.6818	Remote Similarity	NPD1510	Phase 2
0.6816	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7095	Approved
0.6798	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8485	Approved
0.6786	Remote Similarity	NPD1608	Approved
0.678	Remote Similarity	NPD1551	Phase 2
0.6778	Remote Similarity	NPD3887	Approved
0.6778	Remote Similarity	NPD2354	Approved
0.676	Remote Similarity	NPD6674	Discontinued
0.676	Remote Similarity	NPD1243	Approved
0.6746	Remote Similarity	NPD7584	Approved
0.6745	Remote Similarity	NPD8462	Phase 1
0.6743	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD2344	Approved
0.6742	Remote Similarity	NPD7266	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