NPASS Compound

Structure

NPC227879 OpenBabel07101718292D 47 53 0 0 1 0 0 0 0 0999 V2000 3.7624 0.5102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0569 1.5806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8959 -0.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1038 0.6853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1285 1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1225 2.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4533 1.4612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7479 2.5317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1006 1.9965 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4096 1.0454 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1528 0.3763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 7.4170 3.2748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5685 3.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4048 3.2213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7698 2.7396 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2017 0.0672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 32 1 0 0 0 0 4 32 1 0 0 0 0 5 33 1 0 0 0 0 6 33 1 0 0 0 0 7 34 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 36 1 0 0 0 0 13 14 1 0 0 0 0 13 34 1 0 0 0 0 15 18 1 0 0 0 0 16 20 1 0 0 0 0 16 44 1 0 0 0 0 17 36 1 0 0 0 0 17 37 1 0 0 0 0 18 1 1 1 0 0 0 18 25 1 0 0 0 0 19 38 2 0 0 0 0 19 45 1 0 0 0 0 20 26 1 0 0 0 0 20 39 1 1 0 0 0 21 15 1 1 0 0 0 21 45 1 0 0 0 0 22 32 1 0 0 0 0 22 36 1 6 0 0 0 23 35 1 1 0 0 0 23 37 1 0 0 0 0 24 32 1 0 0 0 0 24 46 1 6 0 0 0 25 27 1 0 0 0 0 25 34 1 6 0 0 0 26 28 1 0 0 0 0 26 40 1 6 0 0 0 27 29 1 0 0 0 0 27 41 2 0 0 0 0 28 31 1 0 0 0 0 28 42 1 1 0 0 0 29 35 1 1 0 0 0 29 43 1 0 0 0 0 30 21 1 6 0 0 0 30 33 1 0 0 0 0 30 47 1 0 0 0 0 31 44 1 0 0 0 0 31 46 1 6 0 0 0 33 47 1 0 0 0 0 34 35 1 6 0 0 0 35 8 1 1 0 0 0 36 37 1 1 0 0 0 37 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	662.4
Volume:	671.242
LogP:	3.967
LogD:	2.879
LogS:	-3.637
# Rotatable Bonds:	8
TPSA:	155.28
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.181
Synthetic Accessibility Score:	6.561
Fsp3:	0.946
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:	-5.326
MDCK Permeability:	2.37435942835873e-05
Pgp-inhibitor:	0.866
Pgp-substrate:	0.934
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.701

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	89.35816955566406%
Volume Distribution (VD):	0.919
Pgp-substrate:	7.814636707305908%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.728
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.301
CYP3A4-substrate:	0.275

ADMET: Excretion

Clearance (CL):	1.504
Half-life (T1/2):	0.407

ADMET: Toxicity

hERG Blockers:	0.424
Human Hepatotoxicity (H-HT):	0.278
Drug-inuced Liver Injury (DILI):	0.318
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.757
Maximum Recommended Daily Dose:	0.75
Skin Sensitization:	0.276
Carcinogencity:	0.015
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC227879

Natural Product ID:	NPC227879
*Common Name:**	IHEJMZHKJYHVFF-ZLEXOJGCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IHEJMZHKJYHVFF-ZLEXOJGCSA-N
Standard InCHI:	InChI=1S/C37H58O10/c1-18(15-21(45-19(2)38)30-33(5,6)47-30)25-27(41)29(43)35(8)23-10-9-22-32(3,4)24(46-31-28(42)26(40)20(39)16-44-31)11-12-36(22)17-37(23,36)14-13-34(25,35)7/h18,20-26,28-31,39-40,42-43H,9-17H2,1-8H3/t18-,20-,21-,22+,23+,24+,25+,26+,28-,29+,30-,31+,34-,35-,36-,37+/m1/s1
SMILES:	CC(=O)O[C@@H]([C@H]1OC1(C)C)C[C@H]([C@H]1C(=O)[C@@H]([C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H](C2(C)C)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651282
PubChem CID:	53326834
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[11824572]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124775]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562825]
NPO26366	Actaea pachypoda	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[17253859]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21082802]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21082802]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26366	Actaea pachypoda	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO525	Actaea racemosa	Species	Ranunculaceae	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
EC50	1
Others	2

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Activity	=	1692.0	%	PMID[512532]
NPT2	Others	Unspecified	Activity	=	1947.0	%	PMID[512532]
NPT2	Others	Unspecified	EC50	=	27000.0	nM	PMID[512532]

☑ 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 NPC227879 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	585
0.1-0.2	4158
0.2-0.3	10371
0.3-0.4	12451
0.4-0.5	6253
0.5-0.6	4550
0.6-0.7	3312
0.7-0.8	943
0.8-0.85	56
0.85-0.9	15
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC208333
0.9135	High Similarity	NPC472079
0.9057	High Similarity	NPC473062
0.901	High Similarity	NPC41843
0.8972	High Similarity	NPC477489
0.8932	High Similarity	NPC34562
0.8889	High Similarity	NPC97002
0.8857	High Similarity	NPC203974
0.8812	High Similarity	NPC472273
0.88	High Similarity	NPC470031
0.8738	High Similarity	NPC477172
0.8713	High Similarity	NPC252056
0.8692	High Similarity	NPC236753
0.8692	High Similarity	NPC228190
0.8641	High Similarity	NPC470030
0.8624	High Similarity	NPC477492
0.8614	High Similarity	NPC215570
0.8571	High Similarity	NPC476837
0.8571	High Similarity	NPC139181
0.8571	High Similarity	NPC97260
0.8532	High Similarity	NPC469824
0.8515	High Similarity	NPC191915
0.8515	High Similarity	NPC151214
0.8482	Intermediate Similarity	NPC179429
0.8462	Intermediate Similarity	NPC20028
0.8426	Intermediate Similarity	NPC469826
0.8411	Intermediate Similarity	NPC215408
0.8381	Intermediate Similarity	NPC476838
0.8381	Intermediate Similarity	NPC476512
0.8381	Intermediate Similarity	NPC476839
0.8381	Intermediate Similarity	NPC108227
0.8381	Intermediate Similarity	NPC472081
0.835	Intermediate Similarity	NPC476728
0.8318	Intermediate Similarity	NPC470167
0.8302	Intermediate Similarity	NPC470172
0.8302	Intermediate Similarity	NPC134967
0.8302	Intermediate Similarity	NPC470029
0.8302	Intermediate Similarity	NPC114700
0.8302	Intermediate Similarity	NPC80191
0.8302	Intermediate Similarity	NPC310138
0.8302	Intermediate Similarity	NPC310031
0.8269	Intermediate Similarity	NPC471241
0.8257	Intermediate Similarity	NPC202898
0.8257	Intermediate Similarity	NPC92890
0.8257	Intermediate Similarity	NPC475319
0.8252	Intermediate Similarity	NPC305808
0.8224	Intermediate Similarity	NPC471253
0.8224	Intermediate Similarity	NPC473406
0.8224	Intermediate Similarity	NPC107385
0.8218	Intermediate Similarity	NPC77756
0.8182	Intermediate Similarity	NPC233433
0.8182	Intermediate Similarity	NPC92297
0.8182	Intermediate Similarity	NPC273002
0.8182	Intermediate Similarity	NPC220836
0.8182	Intermediate Similarity	NPC94086
0.8182	Intermediate Similarity	NPC473817
0.8182	Intermediate Similarity	NPC469825
0.8173	Intermediate Similarity	NPC156377
0.8173	Intermediate Similarity	NPC296936
0.8155	Intermediate Similarity	NPC175
0.8155	Intermediate Similarity	NPC30687
0.8148	Intermediate Similarity	NPC469827
0.8148	Intermediate Similarity	NPC88469
0.8142	Intermediate Similarity	NPC79193
0.8095	Intermediate Similarity	NPC74466
0.8095	Intermediate Similarity	NPC470632
0.8095	Intermediate Similarity	NPC470591
0.8077	Intermediate Similarity	NPC94582
0.8077	Intermediate Similarity	NPC473064
0.8077	Intermediate Similarity	NPC473065
0.8077	Intermediate Similarity	NPC473067
0.8077	Intermediate Similarity	NPC57964
0.8073	Intermediate Similarity	NPC306776
0.8073	Intermediate Similarity	NPC166079
0.807	Intermediate Similarity	NPC475490
0.8058	Intermediate Similarity	NPC473726
0.8053	Intermediate Similarity	NPC102619
0.8053	Intermediate Similarity	NPC73986
0.8039	Intermediate Similarity	NPC279329
0.8037	Intermediate Similarity	NPC178853
0.8037	Intermediate Similarity	NPC475574
0.802	Intermediate Similarity	NPC281004
0.8	Intermediate Similarity	NPC238796
0.8	Intermediate Similarity	NPC126753
0.8	Intermediate Similarity	NPC203434
0.8	Intermediate Similarity	NPC237071
0.8	Intermediate Similarity	NPC142264
0.8	Intermediate Similarity	NPC476510
0.7982	Intermediate Similarity	NPC100078
0.7982	Intermediate Similarity	NPC327093
0.7981	Intermediate Similarity	NPC470423
0.7965	Intermediate Similarity	NPC243572
0.7963	Intermediate Similarity	NPC244969
0.7963	Intermediate Similarity	NPC213528
0.7963	Intermediate Similarity	NPC471254
0.7961	Intermediate Similarity	NPC36372
0.7961	Intermediate Similarity	NPC293609
0.7961	Intermediate Similarity	NPC52756
0.7949	Intermediate Similarity	NPC471406
0.7946	Intermediate Similarity	NPC470622
0.7944	Intermediate Similarity	NPC80417
0.7941	Intermediate Similarity	NPC473472
0.7941	Intermediate Similarity	NPC102725
0.7934	Intermediate Similarity	NPC114306
0.7934	Intermediate Similarity	NPC477490
0.7928	Intermediate Similarity	NPC88744
0.7925	Intermediate Similarity	NPC475207
0.7925	Intermediate Similarity	NPC233649
0.7925	Intermediate Similarity	NPC470028
0.7925	Intermediate Similarity	NPC210157
0.7921	Intermediate Similarity	NPC43912
0.7921	Intermediate Similarity	NPC140446
0.7921	Intermediate Similarity	NPC202937
0.7885	Intermediate Similarity	NPC277774
0.7885	Intermediate Similarity	NPC167644
0.7885	Intermediate Similarity	NPC161035
0.7885	Intermediate Similarity	NPC311246
0.7876	Intermediate Similarity	NPC272242
0.7864	Intermediate Similarity	NPC473542
0.7864	Intermediate Similarity	NPC65550
0.7864	Intermediate Similarity	NPC223143
0.7857	Intermediate Similarity	NPC473844
0.7857	Intermediate Similarity	NPC91583
0.7857	Intermediate Similarity	NPC240125
0.7857	Intermediate Similarity	NPC51947
0.7857	Intermediate Similarity	NPC8431
0.783	Intermediate Similarity	NPC475785
0.783	Intermediate Similarity	NPC475765
0.7826	Intermediate Similarity	NPC470115
0.7826	Intermediate Similarity	NPC470116
0.7822	Intermediate Similarity	NPC476727
0.7822	Intermediate Similarity	NPC476726
0.7822	Intermediate Similarity	NPC472272
0.781	Intermediate Similarity	NPC477495
0.781	Intermediate Similarity	NPC473503
0.781	Intermediate Similarity	NPC477224
0.781	Intermediate Similarity	NPC113500
0.781	Intermediate Similarity	NPC309866
0.781	Intermediate Similarity	NPC3538
0.781	Intermediate Similarity	NPC252253
0.781	Intermediate Similarity	NPC45959
0.7805	Intermediate Similarity	NPC477493
0.7798	Intermediate Similarity	NPC94919
0.7798	Intermediate Similarity	NPC80640
0.7797	Intermediate Similarity	NPC472257
0.7788	Intermediate Similarity	NPC476668
0.7788	Intermediate Similarity	NPC5632
0.7788	Intermediate Similarity	NPC59006
0.7788	Intermediate Similarity	NPC473830
0.7788	Intermediate Similarity	NPC473066
0.7788	Intermediate Similarity	NPC106760
0.7788	Intermediate Similarity	NPC204881
0.7788	Intermediate Similarity	NPC149966
0.7788	Intermediate Similarity	NPC473637
0.7788	Intermediate Similarity	NPC471431
0.7778	Intermediate Similarity	NPC239293
0.7769	Intermediate Similarity	NPC273962
0.7768	Intermediate Similarity	NPC230888
0.7768	Intermediate Similarity	NPC316930
0.7767	Intermediate Similarity	NPC131466
0.7767	Intermediate Similarity	NPC82955
0.7748	Intermediate Similarity	NPC119628
0.7748	Intermediate Similarity	NPC158051
0.7748	Intermediate Similarity	NPC158367
0.7736	Intermediate Similarity	NPC287354
0.7736	Intermediate Similarity	NPC17336
0.7736	Intermediate Similarity	NPC469710
0.7736	Intermediate Similarity	NPC92196
0.7736	Intermediate Similarity	NPC62407
0.7731	Intermediate Similarity	NPC470478
0.7723	Intermediate Similarity	NPC290612
0.7719	Intermediate Similarity	NPC11035
0.7719	Intermediate Similarity	NPC204392
0.7719	Intermediate Similarity	NPC91838
0.7719	Intermediate Similarity	NPC275668
0.7719	Intermediate Similarity	NPC274833
0.7719	Intermediate Similarity	NPC1876
0.7719	Intermediate Similarity	NPC240734
0.7714	Intermediate Similarity	NPC476669
0.7714	Intermediate Similarity	NPC172838
0.7714	Intermediate Similarity	NPC474379
0.7714	Intermediate Similarity	NPC472231
0.7714	Intermediate Similarity	NPC472232
0.7714	Intermediate Similarity	NPC137004
0.7714	Intermediate Similarity	NPC88962
0.7714	Intermediate Similarity	NPC149400
0.7714	Intermediate Similarity	NPC144790
0.7714	Intermediate Similarity	NPC476189
0.7712	Intermediate Similarity	NPC178548
0.7712	Intermediate Similarity	NPC258592
0.77	Intermediate Similarity	NPC327451
0.77	Intermediate Similarity	NPC259173
0.77	Intermediate Similarity	NPC472744
0.7699	Intermediate Similarity	NPC87393
0.7699	Intermediate Similarity	NPC320475
0.7699	Intermediate Similarity	NPC477069
0.7699	Intermediate Similarity	NPC477070
0.7699	Intermediate Similarity	NPC321661
0.7692	Intermediate Similarity	NPC156651
0.7692	Intermediate Similarity	NPC473304

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 NPC227879 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	609
0.1-0.2	3983
0.2-0.3	3103
0.3-0.4	820
0.4-0.5	316
0.5-0.6	189
0.6-0.7	123
0.7-0.8	6
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
0.8491	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD8133	Approved
0.7547	Intermediate Similarity	NPD8171	Discontinued
0.75	Intermediate Similarity	NPD7736	Approved
0.748	Intermediate Similarity	NPD7507	Approved
0.7395	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7319	Approved
0.728	Intermediate Similarity	NPD8293	Discontinued
0.7241	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6882	Approved
0.7203	Intermediate Similarity	NPD8297	Approved
0.7177	Intermediate Similarity	NPD8328	Phase 3
0.71	Intermediate Similarity	NPD6116	Phase 1
0.7097	Intermediate Similarity	NPD6370	Approved
0.708	Intermediate Similarity	NPD1700	Approved
0.7069	Intermediate Similarity	NPD6412	Phase 2
0.703	Intermediate Similarity	NPD6697	Approved
0.703	Intermediate Similarity	NPD6114	Approved
0.703	Intermediate Similarity	NPD6115	Approved
0.703	Intermediate Similarity	NPD6118	Approved
0.7025	Intermediate Similarity	NPD6940	Discontinued
0.7	Intermediate Similarity	NPD6117	Approved
0.6984	Remote Similarity	NPD7492	Approved
0.6983	Remote Similarity	NPD7128	Approved
0.6983	Remote Similarity	NPD6675	Approved
0.6983	Remote Similarity	NPD5739	Approved
0.6983	Remote Similarity	NPD6402	Approved
0.6967	Remote Similarity	NPD6009	Approved
0.6949	Remote Similarity	NPD6372	Approved
0.6949	Remote Similarity	NPD6373	Approved
0.6935	Remote Similarity	NPD8294	Approved
0.6935	Remote Similarity	NPD6054	Approved
0.6935	Remote Similarity	NPD6059	Approved
0.6935	Remote Similarity	NPD8377	Approved
0.6935	Remote Similarity	NPD6319	Approved
0.6929	Remote Similarity	NPD6616	Approved
0.6911	Remote Similarity	NPD7328	Approved
0.6911	Remote Similarity	NPD7327	Approved
0.69	Remote Similarity	NPD3702	Approved
0.6893	Remote Similarity	NPD6928	Phase 2
0.688	Remote Similarity	NPD8379	Approved
0.688	Remote Similarity	NPD8378	Approved
0.688	Remote Similarity	NPD8296	Approved
0.688	Remote Similarity	NPD8380	Approved
0.688	Remote Similarity	NPD8033	Approved
0.688	Remote Similarity	NPD8335	Approved
0.6875	Remote Similarity	NPD7078	Approved
0.6864	Remote Similarity	NPD6899	Approved
0.6864	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7320	Approved
0.6864	Remote Similarity	NPD6881	Approved
0.686	Remote Similarity	NPD4632	Approved
0.6855	Remote Similarity	NPD7516	Approved
0.6833	Remote Similarity	NPD6650	Approved
0.6833	Remote Similarity	NPD8130	Phase 1
0.6833	Remote Similarity	NPD6649	Approved
0.68	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5697	Approved
0.678	Remote Similarity	NPD5701	Approved
0.6772	Remote Similarity	NPD7604	Phase 2
0.6752	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6883	Approved
0.675	Remote Similarity	NPD7290	Approved
0.675	Remote Similarity	NPD7102	Approved
0.6746	Remote Similarity	NPD6016	Approved
0.6746	Remote Similarity	NPD6015	Approved
0.6733	Remote Similarity	NPD3703	Phase 2
0.6694	Remote Similarity	NPD6847	Approved
0.6694	Remote Similarity	NPD6617	Approved
0.6694	Remote Similarity	NPD6869	Approved
0.6693	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD8035	Phase 2
0.66	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5777	Approved
0.6583	Remote Similarity	NPD6011	Approved
0.6557	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD3669	Approved
0.6542	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4755	Approved
0.6509	Remote Similarity	NPD1780	Approved
0.6509	Remote Similarity	NPD1779	Approved
0.65	Remote Similarity	NPD4244	Approved
0.65	Remote Similarity	NPD4245	Approved
0.65	Remote Similarity	NPD4789	Approved
0.6484	Remote Similarity	NPD7503	Approved
0.6484	Remote Similarity	NPD5983	Phase 2
0.6446	Remote Similarity	NPD6686	Approved
0.6439	Remote Similarity	NPD6033	Approved
0.6422	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6008	Approved
0.6412	Remote Similarity	NPD6336	Discontinued
0.641	Remote Similarity	NPD5285	Approved
0.641	Remote Similarity	NPD4696	Approved
0.641	Remote Similarity	NPD4700	Approved
0.641	Remote Similarity	NPD5286	Approved
0.64	Remote Similarity	NPD3698	Phase 2
0.64	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6083	Phase 2
0.6379	Remote Similarity	NPD6084	Phase 2
0.6357	Remote Similarity	NPD6921	Approved
0.6349	Remote Similarity	NPD6274	Approved
0.6341	Remote Similarity	NPD4634	Approved
0.6328	Remote Similarity	NPD7100	Approved
0.6328	Remote Similarity	NPD7101	Approved
0.6303	Remote Similarity	NPD5225	Approved
0.6303	Remote Similarity	NPD4633	Approved
0.6303	Remote Similarity	NPD5226	Approved
0.6303	Remote Similarity	NPD5224	Approved
0.6303	Remote Similarity	NPD5211	Phase 2
0.63	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5360	Phase 3
0.6299	Remote Similarity	NPD7115	Discovery
0.6281	Remote Similarity	NPD4768	Approved
0.6281	Remote Similarity	NPD4767	Approved
0.6275	Remote Similarity	NPD6081	Approved
0.625	Remote Similarity	NPD6335	Approved
0.625	Remote Similarity	NPD5174	Approved
0.625	Remote Similarity	NPD5175	Approved
0.6231	Remote Similarity	NPD6909	Approved
0.6231	Remote Similarity	NPD6908	Approved
0.6218	Remote Similarity	NPD5223	Approved
0.621	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7991	Discontinued
0.6198	Remote Similarity	NPD5141	Approved
0.6179	Remote Similarity	NPD4730	Approved
0.6179	Remote Similarity	NPD4729	Approved
0.6172	Remote Similarity	NPD6317	Approved
0.6167	Remote Similarity	NPD8086	Approved
0.6167	Remote Similarity	NPD8084	Approved
0.6167	Remote Similarity	NPD8082	Approved
0.6167	Remote Similarity	NPD8139	Approved
0.6167	Remote Similarity	NPD8085	Approved
0.6167	Remote Similarity	NPD8138	Approved
0.6167	Remote Similarity	NPD8083	Approved
0.6136	Remote Similarity	NPD6067	Discontinued
0.6124	Remote Similarity	NPD6313	Approved
0.6124	Remote Similarity	NPD6314	Approved
0.6116	Remote Similarity	NPD4754	Approved
0.6116	Remote Similarity	NPD8276	Approved
0.6116	Remote Similarity	NPD8275	Approved
0.6107	Remote Similarity	NPD8513	Phase 3
0.6107	Remote Similarity	NPD8515	Approved
0.6107	Remote Similarity	NPD8516	Approved
0.6107	Remote Similarity	NPD8517	Approved
0.61	Remote Similarity	NPD4224	Phase 2
0.608	Remote Similarity	NPD5250	Approved
0.608	Remote Similarity	NPD5251	Approved
0.608	Remote Similarity	NPD5248	Approved
0.608	Remote Similarity	NPD5249	Phase 3
0.608	Remote Similarity	NPD5247	Approved
0.6068	Remote Similarity	NPD5695	Phase 3
0.6066	Remote Similarity	NPD8081	Approved
0.605	Remote Similarity	NPD5696	Approved
0.605	Remote Similarity	NPD7638	Approved
0.6048	Remote Similarity	NPD5128	Approved
0.6034	Remote Similarity	NPD6399	Phase 3
0.6033	Remote Similarity	NPD8300	Approved
0.6033	Remote Similarity	NPD8301	Approved
0.6016	Remote Similarity	NPD8393	Approved
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD8418	Phase 2
0.6	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1811	Approved
0.6	Remote Similarity	NPD7639	Approved
0.6	Remote Similarity	NPD1810	Approved
0.5985	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD7748	Approved
0.5968	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7902	Approved
0.5962	Remote Similarity	NPD4758	Discontinued
0.5946	Remote Similarity	NPD4788	Approved
0.5932	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5364	Discontinued
0.5926	Remote Similarity	NPD4238	Approved
0.5926	Remote Similarity	NPD3671	Phase 1
0.5926	Remote Similarity	NPD4802	Phase 2
0.5913	Remote Similarity	NPD4753	Phase 2
0.5913	Remote Similarity	NPD5328	Approved
0.5906	Remote Similarity	NPD5215	Approved
0.5906	Remote Similarity	NPD5216	Approved
0.5906	Remote Similarity	NPD5217	Approved
0.5902	Remote Similarity	NPD7632	Discontinued
0.5897	Remote Similarity	NPD4202	Approved
0.5882	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4697	Phase 3
0.5882	Remote Similarity	NPD5221	Approved
0.5882	Remote Similarity	NPD5222	Approved
0.5872	Remote Similarity	NPD7329	Approved
0.5865	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD4787	Phase 1
0.5846	Remote Similarity	NPD6868	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