NPASS Compound

Structure

NPC311357 OpenBabel07101718332D 58 62 0 0 1 0 0 0 0 0999 V2000 -10.1370 -5.3522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4949 -6.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1241 0.5891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4450 -1.6987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9217 -4.8875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.0969 -0.3025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.3477 -1.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1612 -0.0518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6752 1.2625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9468 0.6238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6626 -1.9233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4762 -0.7368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5925 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1358 -0.3264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 -3.3906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3558 -1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6779 -2.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4734 -5.5713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3569 -3.0425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0338 -3.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3685 -5.9420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5344 -0.1795 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.7269 -1.6725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3558 -2.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6779 -1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7815 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0532 -0.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3470 -4.6108 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.4211 -2.7918 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8727 -3.3906 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8390 1.4531 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6779 0.9687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6779 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6989 0.3124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5613 -2.4733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9927 -3.6607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1731 -0.9078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3803 -4.5474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 -0.4844 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6655 0.2490 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.6247 -1.5066 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.2643 -4.2994 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.4845 -1.8251 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.5115 -4.1190 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 2.4219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 2.4219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 1.4531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 -0.4844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5724 1.2728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6009 -2.5997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7612 -4.2504 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0121 -0.4234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1296 -5.4832 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 -1.4531 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 23 1 0 0 0 0 2 23 1 0 0 0 0 4 46 1 0 0 0 0 5 47 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 25 2 0 0 0 0 12 25 1 0 0 0 0 13 28 2 0 0 0 0 14 29 2 0 0 0 0 15 17 1 0 0 0 0 15 26 2 0 0 0 0 16 18 2 0 0 0 0 16 26 1 0 0 0 0 17 27 2 0 0 0 0 18 27 1 0 0 0 0 19 23 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 22 48 1 0 0 0 0 24 3 1 6 0 0 0 24 40 1 0 0 0 0 24 43 1 0 0 0 0 27 57 1 0 0 0 0 28 29 1 0 0 0 0 28 37 1 0 0 0 0 29 44 1 0 0 0 0 30 19 1 6 0 0 0 30 41 1 0 0 0 0 30 45 1 0 0 0 0 31 20 1 6 0 0 0 31 39 1 0 0 0 0 31 46 1 0 0 0 0 32 21 1 6 0 0 0 32 38 1 0 0 0 0 32 47 1 0 0 0 0 33 22 1 1 0 0 0 33 34 1 0 0 0 0 33 58 1 0 0 0 0 34 35 1 0 0 0 0 34 49 1 6 0 0 0 35 36 1 0 0 0 0 35 50 1 1 0 0 0 36 42 1 0 0 0 0 36 51 1 6 0 0 0 37 43 2 3 0 0 0 37 52 1 0 0 0 0 38 44 2 3 0 0 0 38 53 1 0 0 0 0 39 45 2 3 0 0 0 39 54 1 0 0 0 0 40 46 1 0 0 0 0 40 55 2 0 0 0 0 41 47 1 0 0 0 0 41 56 2 0 0 0 0 42 57 1 1 0 0 0 42 58 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	803.37
Volume:	806.971
LogP:	2.243
LogD:	2.21
LogS:	-4.302
# Rotatable Bonds:	9
TPSA:	227.3
# H-Bond Aceptor:	16
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.159
Synthetic Accessibility Score:	5.359
Fsp3:	0.452
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.239
MDCK Permeability:	9.265266271540895e-06
Pgp-inhibitor:	0.995
Pgp-substrate:	0.893
Human Intestinal Absorption (HIA):	0.637
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.06
Plasma Protein Binding (PPB):	87.7785415649414%
Volume Distribution (VD):	0.583
Pgp-substrate:	5.5506792068481445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.039
CYP2C19-inhibitor:	0.142
CYP2C19-substrate:	0.407
CYP2C9-inhibitor:	0.535
CYP2C9-substrate:	0.48
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.189
CYP3A4-inhibitor:	0.882
CYP3A4-substrate:	0.469

ADMET: Excretion

Clearance (CL):	1.297
Half-life (T1/2):	0.316

ADMET: Toxicity

hERG Blockers:	0.166
Human Hepatotoxicity (H-HT):	0.92
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.673
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.043
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.011

Download Data

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

Natural Product: NPC311357

Natural Product ID:	NPC311357
*Common Name:**	Cycloaspeptide F
IUPAC Name:	(4S,7S,10S,13S)-7-benzyl-4,6,12-trimethyl-10-(2-methylpropyl)-13-[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]-3,6,9,12,15-pentazabicyclo[14.4.0]icosa-1(20),16,18-triene-2,5,8,11,14-pentone
Synonyms:	Cycloaspeptide F
Standard InCHIKey:	HGCDDJBOTFSYBL-HEZYXVPISA-N
Standard InCHI:	InChI=1S/C42H53N5O11/c1-23(2)19-30-41(56)47(5)32(21-26-15-17-27(18-16-26)57-42-36(51)35(50)34(49)33(22-48)58-42)38(53)44-29-14-10-9-13-28(29)37(52)43-24(3)40(55)46(4)31(39(54)45-30)20-25-11-7-6-8-12-25/h6-18,23-24,30-36,42,48-51H,19-22H2,1-5H3,(H,43,52)(H,44,53)(H,45,54)/t24-,30-,31-,32-,33+,34+,35-,36+,42+/m0/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(cc2)C[C@H]2C(=Nc3ccccc3C(=N[C@@H](C)C(=O)N([C@H](C(=N[C@H](C(=O)N2C)CC(C)C)O)Cc2ccccc2)C)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL553621
PubChem CID:	44234959
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO10809	Isaria farinosa	Species	Cordycipitaceae	Eukaryota	Cordyceps-colonizing isolate of Isaria farinosa	n.a.	n.a.	PMID[19572613]
NPO10809	Isaria farinosa	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21158423]
NPO10809	Isaria farinosa	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21495659]
NPO10809	Isaria farinosa	Species	Cordycipitaceae	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
GI50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	49800.0	nM	PMID[539124]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	18700.0	nM	PMID[539124]

☑ 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 NPC311357 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	260
0.1-0.2	1331
0.2-0.3	5983
0.3-0.4	10897
0.4-0.5	8433
0.5-0.6	13292
0.6-0.7	2326
0.7-0.8	162
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8385	Intermediate Similarity	NPC144314
0.8342	Intermediate Similarity	NPC50548
0.8333	Intermediate Similarity	NPC149962
0.8299	Intermediate Similarity	NPC123859
0.8167	Intermediate Similarity	NPC289776
0.8167	Intermediate Similarity	NPC133470
0.8167	Intermediate Similarity	NPC191863
0.8163	Intermediate Similarity	NPC242728
0.7941	Intermediate Similarity	NPC326333
0.7865	Intermediate Similarity	NPC315542
0.7864	Intermediate Similarity	NPC326027
0.7861	Intermediate Similarity	NPC473460
0.7688	Intermediate Similarity	NPC254700
0.767	Intermediate Similarity	NPC471561
0.7665	Intermediate Similarity	NPC473407
0.7665	Intermediate Similarity	NPC473378
0.7654	Intermediate Similarity	NPC254798
0.7647	Intermediate Similarity	NPC473422
0.7593	Intermediate Similarity	NPC248903
0.757	Intermediate Similarity	NPC148124
0.7551	Intermediate Similarity	NPC276120
0.7551	Intermediate Similarity	NPC291759
0.7546	Intermediate Similarity	NPC26928
0.7539	Intermediate Similarity	NPC158277
0.7538	Intermediate Similarity	NPC294951
0.7525	Intermediate Similarity	NPC29531
0.7523	Intermediate Similarity	NPC99724
0.75	Intermediate Similarity	NPC133591
0.7487	Intermediate Similarity	NPC248670
0.7474	Intermediate Similarity	NPC32064
0.7474	Intermediate Similarity	NPC196091
0.7459	Intermediate Similarity	NPC140915
0.7459	Intermediate Similarity	NPC18249
0.7459	Intermediate Similarity	NPC197741
0.7459	Intermediate Similarity	NPC187028
0.7459	Intermediate Similarity	NPC10221
0.7459	Intermediate Similarity	NPC305700
0.7459	Intermediate Similarity	NPC245974
0.7453	Intermediate Similarity	NPC471531
0.7448	Intermediate Similarity	NPC473402
0.7448	Intermediate Similarity	NPC164608
0.7435	Intermediate Similarity	NPC230611
0.7432	Intermediate Similarity	NPC139699
0.7432	Intermediate Similarity	NPC114659
0.7429	Intermediate Similarity	NPC471532
0.7423	Intermediate Similarity	NPC45037
0.7421	Intermediate Similarity	NPC186617
0.7389	Intermediate Similarity	NPC178466
0.7389	Intermediate Similarity	NPC63628
0.7382	Intermediate Similarity	NPC471568
0.7382	Intermediate Similarity	NPC473693
0.7376	Intermediate Similarity	NPC471563
0.7374	Intermediate Similarity	NPC38823
0.7374	Intermediate Similarity	NPC207033
0.7366	Intermediate Similarity	NPC56635
0.736	Intermediate Similarity	NPC471048
0.736	Intermediate Similarity	NPC471050
0.736	Intermediate Similarity	NPC471049
0.7358	Intermediate Similarity	NPC279871
0.7358	Intermediate Similarity	NPC473354
0.7358	Intermediate Similarity	NPC159767
0.7358	Intermediate Similarity	NPC471165
0.7358	Intermediate Similarity	NPC155506
0.735	Intermediate Similarity	NPC473305
0.735	Intermediate Similarity	NPC163961
0.7348	Intermediate Similarity	NPC247298
0.734	Intermediate Similarity	NPC320064
0.7333	Intermediate Similarity	NPC269750
0.7333	Intermediate Similarity	NPC194671
0.7323	Intermediate Similarity	NPC138083
0.732	Intermediate Similarity	NPC50016
0.731	Intermediate Similarity	NPC471526
0.7306	Intermediate Similarity	NPC273755
0.7292	Intermediate Similarity	NPC40234
0.7277	Intermediate Similarity	NPC107938
0.7277	Intermediate Similarity	NPC294516
0.7264	Intermediate Similarity	NPC64140
0.7264	Intermediate Similarity	NPC174122
0.7263	Intermediate Similarity	NPC472923
0.7243	Intermediate Similarity	NPC314817
0.7243	Intermediate Similarity	NPC316297
0.7243	Intermediate Similarity	NPC66191
0.7228	Intermediate Similarity	NPC477526
0.7222	Intermediate Similarity	NPC469831
0.7214	Intermediate Similarity	NPC234069
0.7213	Intermediate Similarity	NPC9373
0.7186	Intermediate Similarity	NPC469829
0.7184	Intermediate Similarity	NPC323662
0.7182	Intermediate Similarity	NPC195814
0.7179	Intermediate Similarity	NPC476227
0.7177	Intermediate Similarity	NPC159101
0.7172	Intermediate Similarity	NPC476321
0.7165	Intermediate Similarity	NPC89831
0.7164	Intermediate Similarity	NPC469830
0.7163	Intermediate Similarity	NPC214368
0.7157	Intermediate Similarity	NPC328763
0.7156	Intermediate Similarity	NPC274268
0.7143	Intermediate Similarity	NPC287757
0.7143	Intermediate Similarity	NPC319320
0.7128	Intermediate Similarity	NPC306804
0.7127	Intermediate Similarity	NPC189724
0.7127	Intermediate Similarity	NPC212850
0.7127	Intermediate Similarity	NPC83289
0.7106	Intermediate Similarity	NPC472435
0.7098	Intermediate Similarity	NPC473502
0.7092	Intermediate Similarity	NPC26108
0.709	Intermediate Similarity	NPC10730
0.709	Intermediate Similarity	NPC10875
0.709	Intermediate Similarity	NPC212699
0.709	Intermediate Similarity	NPC207675
0.7089	Intermediate Similarity	NPC472436
0.7081	Intermediate Similarity	NPC132771
0.7075	Intermediate Similarity	NPC257266
0.7074	Intermediate Similarity	NPC99891
0.7071	Intermediate Similarity	NPC475421
0.7056	Intermediate Similarity	NPC472434
0.7042	Intermediate Similarity	NPC257728
0.7041	Intermediate Similarity	NPC137627
0.7032	Intermediate Similarity	NPC108826
0.7016	Intermediate Similarity	NPC476194
0.7015	Intermediate Similarity	NPC315913
0.7009	Intermediate Similarity	NPC153365
0.7005	Intermediate Similarity	NPC233702
0.7	Intermediate Similarity	NPC314025
0.6973	Remote Similarity	NPC161155
0.6973	Remote Similarity	NPC97004
0.6973	Remote Similarity	NPC136951
0.6965	Remote Similarity	NPC314213
0.6965	Remote Similarity	NPC314656
0.6965	Remote Similarity	NPC470903
0.6965	Remote Similarity	NPC167763
0.6965	Remote Similarity	NPC470112
0.6957	Remote Similarity	NPC184933
0.6957	Remote Similarity	NPC59827
0.6952	Remote Similarity	NPC473491
0.6952	Remote Similarity	NPC476743
0.6939	Remote Similarity	NPC475204
0.6939	Remote Similarity	NPC475123
0.6939	Remote Similarity	NPC46009
0.6938	Remote Similarity	NPC477550
0.6938	Remote Similarity	NPC477552
0.6935	Remote Similarity	NPC97282
0.6935	Remote Similarity	NPC313414
0.6927	Remote Similarity	NPC174629
0.6923	Remote Similarity	NPC328649
0.6919	Remote Similarity	NPC472330
0.6919	Remote Similarity	NPC472329
0.6916	Remote Similarity	NPC79130
0.6915	Remote Similarity	NPC471032
0.6915	Remote Similarity	NPC470935
0.6915	Remote Similarity	NPC476744
0.6912	Remote Similarity	NPC94862
0.6907	Remote Similarity	NPC63931
0.6905	Remote Similarity	NPC267414
0.6897	Remote Similarity	NPC299806
0.6895	Remote Similarity	NPC476268
0.6891	Remote Similarity	NPC19023
0.689	Remote Similarity	NPC471592
0.6885	Remote Similarity	NPC36434
0.6872	Remote Similarity	NPC50380
0.6872	Remote Similarity	NPC179250
0.6872	Remote Similarity	NPC477551
0.6872	Remote Similarity	NPC475654
0.6867	Remote Similarity	NPC291609
0.6862	Remote Similarity	NPC324081
0.686	Remote Similarity	NPC204970
0.6857	Remote Similarity	NPC477527
0.6852	Remote Similarity	NPC293347
0.6848	Remote Similarity	NPC298821
0.6845	Remote Similarity	NPC283207
0.6842	Remote Similarity	NPC476742
0.6839	Remote Similarity	NPC471203
0.6834	Remote Similarity	NPC136797
0.683	Remote Similarity	NPC475292
0.683	Remote Similarity	NPC475442
0.683	Remote Similarity	NPC475565
0.683	Remote Similarity	NPC475349
0.6828	Remote Similarity	NPC81026
0.6827	Remote Similarity	NPC471825
0.6824	Remote Similarity	NPC124300
0.6822	Remote Similarity	NPC14339
0.6818	Remote Similarity	NPC328494
0.6812	Remote Similarity	NPC248822
0.6811	Remote Similarity	NPC123761
0.6809	Remote Similarity	NPC310618
0.6806	Remote Similarity	NPC476741
0.6802	Remote Similarity	NPC470936
0.68	Remote Similarity	NPC168153
0.6791	Remote Similarity	NPC16188
0.6789	Remote Similarity	NPC262166
0.6788	Remote Similarity	NPC244336
0.678	Remote Similarity	NPC262725
0.6774	Remote Similarity	NPC266741
0.6774	Remote Similarity	NPC477160
0.6769	Remote Similarity	NPC57105
0.6769	Remote Similarity	NPC54803
0.6769	Remote Similarity	NPC321592
0.6768	Remote Similarity	NPC90984
0.6763	Remote Similarity	NPC61332
0.6763	Remote Similarity	NPC240130

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 NPC311357 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	486
0.2-0.3	877
0.3-0.4	1466
0.4-0.5	2588
0.5-0.6	2754
0.6-0.7	788
0.7-0.8	26
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
0.7527	Intermediate Similarity	NPD7131	Phase 3
0.7488	Intermediate Similarity	NPD7810	Phase 3
0.7488	Intermediate Similarity	NPD7811	Phase 3
0.7433	Intermediate Similarity	NPD6063	Approved
0.7296	Intermediate Similarity	NPD6211	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7608	Discontinued
0.7214	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD8031	Discontinued
0.7169	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2215	Approved
0.7165	Intermediate Similarity	NPD2216	Approved
0.715	Intermediate Similarity	NPD6874	Approved
0.7136	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6519	Phase 2
0.7095	Intermediate Similarity	NPD6669	Phase 2
0.7087	Intermediate Similarity	NPD5582	Discontinued
0.7079	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7583	Approved
0.7075	Intermediate Similarity	NPD7263	Phase 2
0.7062	Intermediate Similarity	NPD7485	Phase 3
0.7062	Intermediate Similarity	NPD7484	Phase 3
0.7053	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5558	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7585	Approved
0.7026	Intermediate Similarity	NPD8359	Phase 2
0.7016	Intermediate Similarity	NPD5773	Approved
0.7016	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5772	Approved
0.7005	Intermediate Similarity	NPD5938	Phase 3
0.7005	Intermediate Similarity	NPD6550	Discontinued
0.7	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD7426	Phase 1
0.6995	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5150	Phase 2
0.6981	Remote Similarity	NPD7891	Discontinued
0.6935	Remote Similarity	NPD3965	Phase 1
0.6933	Remote Similarity	NPD8255	Phase 2
0.6923	Remote Similarity	NPD2904	Discontinued
0.6916	Remote Similarity	NPD7584	Approved
0.6915	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD3778	Approved
0.6907	Remote Similarity	NPD8070	Approved
0.6903	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6045	Phase 3
0.6895	Remote Similarity	NPD8149	Discontinued
0.6891	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD3560	Approved
0.6891	Remote Similarity	NPD3558	Approved
0.6891	Remote Similarity	NPD3556	Approved
0.6891	Remote Similarity	NPD3557	Approved
0.689	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD8025	Phase 2
0.6878	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7256	Discontinued
0.6869	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3153	Approved
0.6863	Remote Similarity	NPD3154	Approved
0.6862	Remote Similarity	NPD4123	Phase 3
0.6854	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7546	Discontinued
0.6845	Remote Similarity	NPD2843	Phase 2
0.6845	Remote Similarity	NPD2845	Phase 2
0.6844	Remote Similarity	NPD5640	Discontinued
0.6842	Remote Similarity	NPD4003	Phase 3
0.6842	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7967	Discontinued
0.6837	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7043	Discontinued
0.6828	Remote Similarity	NPD5481	Discontinued
0.6825	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2388	Discontinued
0.681	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5811	Approved
0.6789	Remote Similarity	NPD2122	Discontinued
0.6789	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8311	Discontinued
0.6782	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6339	Approved
0.678	Remote Similarity	NPD6340	Approved
0.6776	Remote Similarity	NPD3802	Phase 3
0.6771	Remote Similarity	NPD4678	Approved
0.6771	Remote Similarity	NPD8479	Phase 2
0.6771	Remote Similarity	NPD4675	Approved
0.6762	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7476	Discontinued
0.6758	Remote Similarity	NPD7827	Phase 1
0.6756	Remote Similarity	NPD7820	Phase 3
0.675	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7262	Phase 1
0.6744	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5561	Approved
0.6742	Remote Similarity	NPD5562	Approved
0.6741	Remote Similarity	NPD6298	Discontinued
0.674	Remote Similarity	NPD8059	Phase 3
0.674	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD4083	Discontinued
0.673	Remote Similarity	NPD4604	Approved
0.673	Remote Similarity	NPD6034	Phase 2
0.673	Remote Similarity	NPD4605	Approved
0.672	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7318	Phase 3
0.6717	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD8161	Suspended
0.6702	Remote Similarity	NPD8323	Discontinued
0.6701	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3823	Discontinued
0.67	Remote Similarity	NPD3953	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3952	Approved
0.67	Remote Similarity	NPD3951	Phase 3
0.67	Remote Similarity	NPD7007	Discovery
0.6699	Remote Similarity	NPD4372	Phase 1
0.6696	Remote Similarity	NPD7797	Approved
0.6696	Remote Similarity	NPD7224	Discontinued
0.6696	Remote Similarity	NPD7796	Approved
0.6696	Remote Similarity	NPD7223	Discontinued
0.6694	Remote Similarity	NPD8461	Discontinued
0.6684	Remote Similarity	NPD3536	Discontinued
0.6684	Remote Similarity	NPD6502	Phase 2
0.6683	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7281	Phase 3
0.6683	Remote Similarity	NPD5847	Phase 1
0.6683	Remote Similarity	NPD7280	Phase 3
0.6682	Remote Similarity	NPD5512	Phase 3
0.6682	Remote Similarity	NPD7225	Discontinued
0.6681	Remote Similarity	NPD6716	Phase 1
0.6681	Remote Similarity	NPD7853	Phase 2
0.6667	Remote Similarity	NPD4515	Suspended
0.6667	Remote Similarity	NPD7565	Approved
0.6667	Remote Similarity	NPD7972	Discontinued
0.6667	Remote Similarity	NPD7859	Phase 2
0.6652	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6851	Approved
0.665	Remote Similarity	NPD5604	Discontinued
0.665	Remote Similarity	NPD6853	Approved
0.665	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6072	Discontinued
0.6649	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5745	Approved
0.6648	Remote Similarity	NPD7477	Discontinued
0.6634	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD2821	Approved
0.6633	Remote Similarity	NPD6457	Approved
0.6632	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3263	Phase 3
0.6623	Remote Similarity	NPD4885	Approved
0.6618	Remote Similarity	NPD6184	Discontinued
0.6618	Remote Similarity	NPD5553	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7317	Phase 3
0.6606	Remote Similarity	NPD5429	Discontinued
0.6606	Remote Similarity	NPD7222	Phase 2
0.6606	Remote Similarity	NPD6296	Discontinued
0.6603	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7877	Suspended
0.66	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2995	Approved
0.6598	Remote Similarity	NPD3296	Phase 1
0.6598	Remote Similarity	NPD8417	Discontinued
0.6597	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7558	Phase 2
0.6594	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7556	Discontinued
0.6593	Remote Similarity	NPD7805	Phase 3
0.6588	Remote Similarity	NPD5984	Phase 2
0.6587	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4204	Approved
0.6585	Remote Similarity	NPD4203	Approved
0.6585	Remote Similarity	NPD3037	Phase 1
0.6579	Remote Similarity	NPD5756	Phase 2
0.6578	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7194	Discontinued
0.6575	Remote Similarity	NPD8027	Approved
0.6575	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD2498	Approved
0.6573	Remote Similarity	NPD7491	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5641	Discontinued
0.6571	Remote Similarity	NPD5994	Discontinued
0.657	Remote Similarity	NPD8463	Approved
0.657	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5557	Phase 1
0.6569	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD8356	Approved
0.6564	Remote Similarity	NPD6677	Suspended
0.6562	Remote Similarity	NPD7823	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