NPASS Compound

Structure

NPC253987 OpenBabel07101718282D 52 59 0 0 1 0 0 0 0 0999 V2000 1.2521 1.1177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8239 -1.1476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9182 -0.1952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2254 3.2983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2892 1.3323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8700 -2.8073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2254 -2.7610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1206 -0.7727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6961 -0.5267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9335 -1.2420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4824 -1.0068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1206 0.1660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3872 -0.1016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7465 -0.7727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9598 -1.0617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6178 1.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0622 1.6516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0900 0.3248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1600 -1.9146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6178 -0.8503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6630 -0.9601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1287 1.5535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9335 0.6354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8646 -0.1565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7465 0.1660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6509 -0.6366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4440 -0.2569 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.5372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8195 -0.3320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4392 -0.1111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0210 -1.0510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5557 0.2686 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2185 1.0280 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3085 -0.1660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5319 -1.2170 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2185 -0.4908 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4392 0.6483 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9312 -0.8575 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1283 -0.6915 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4440 0.7941 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9093 -0.5255 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.0782 -1.7194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9182 0.7324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5171 0.2961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2521 -0.5804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3234 -1.6791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1287 -1.0163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4995 2.4005 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -5.0940 0.4141 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -3.2419 -2.1097 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -1.4995 -1.8633 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 37 1 0 0 0 0 2 38 1 0 0 0 0 3 39 1 0 0 0 0 4 49 1 0 0 0 0 5 50 1 0 0 0 0 6 51 1 0 0 0 0 7 52 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 23 2 0 0 0 0 13 24 2 0 0 0 0 14 25 2 0 0 0 0 15 26 2 0 0 0 0 16 22 1 0 0 0 0 16 33 1 0 0 0 0 17 22 2 0 0 0 0 17 41 1 0 0 0 0 18 34 1 0 0 0 0 19 43 1 0 0 0 0 20 36 1 0 0 0 0 20 48 1 0 0 0 0 21 40 1 0 0 0 0 21 48 1 0 0 0 0 22 23 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 24 32 1 0 0 0 0 25 41 1 0 0 0 0 26 40 1 0 0 0 0 27 32 1 6 0 0 0 27 40 1 0 0 0 0 27 42 1 0 0 0 0 28 33 1 0 0 0 0 28 39 1 0 0 0 0 28 44 2 0 0 0 0 29 34 1 0 0 0 0 29 38 1 0 0 0 0 29 45 2 0 0 0 0 30 36 1 0 0 0 0 30 37 1 0 0 0 0 30 46 2 0 0 0 0 31 35 1 0 0 0 0 31 42 1 0 0 0 0 31 47 2 0 0 0 0 32 18 1 1 0 0 0 32 41 1 0 0 0 0 33 37 1 0 0 0 0 33 49 1 6 0 0 0 34 42 1 0 0 0 0 34 50 1 6 0 0 0 35 19 1 1 0 0 0 35 38 1 0 0 0 0 35 51 1 0 0 0 0 36 39 1 0 0 0 0 36 52 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	782.2
Volume:	726.517
LogP:	5.145
LogD:	2.324
LogS:	-5.209
# Rotatable Bonds:	5
TPSA:	118.87
# H-Bond Aceptor:	12
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.412
Synthetic Accessibility Score:	7.751
Fsp3:	0.5
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:	-5.451
MDCK Permeability:	1.3621872312796768e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.779
Human Intestinal Absorption (HIA):	0.783
20% Bioavailability (F20%):	0.586
30% Bioavailability (F30%):	0.91

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.373
Plasma Protein Binding (PPB):	95.21968841552734%
Volume Distribution (VD):	1.661
Pgp-substrate:	2.6540679931640625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.58
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.979
CYP2C9-inhibitor:	0.962
CYP2C9-substrate:	0.111
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.017
CYP3A4-inhibitor:	0.967
CYP3A4-substrate:	0.994

ADMET: Excretion

Clearance (CL):	9.151
Half-life (T1/2):	0.004

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.803
Drug-inuced Liver Injury (DILI):	0.996
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.802
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.909
Carcinogencity:	0.654
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.0

Download Data

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

Natural Product: NPC253987

Natural Product ID:	NPC253987
*Common Name:**	Chaetocochin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DOTYKRRRMXXIPL-ISYIGULMSA-N
Standard InCHI:	InChI=1S/C36H42N6O6S4/c1-37-30(46)36(52-7)20-48-21-40-26-15-11-9-13-24(26)32(18-34(50-5)29(45)38(2)35(19-43,51-6)31(47)42(34)27(32)40)41-17-22(23-12-8-10-14-25(23)41)16-33(37,49-4)28(44)39(36)3/h8-15,17,27,43H,16,18-21H2,1-7H3/t27-,32+,33+,34+,35+,36+/m1/s1
SMILES:	CS[C@@]12C[C@@]34[C@@H](N2C(=O)[C@](N(C1=O)C)(CO)SC)N(c1c3cccc1)COC[C@@]1(SC)N(C(=O)[C@](Cc2cn4c3ccccc23)(SC)N(C1=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454044
PubChem CID:	16086610
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000064] Macrolactams

*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
NPO9444	Chaetomium cochliodes	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989540]
NPO9444	Chaetomium cochliodes	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32115958]
NPO9444	Chaetomium cochliodes	Species	Chaetomiaceae	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	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	4.1	ug.mL-1	PMID[543731]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	3.4	ug.mL-1	PMID[543731]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	7.0	ug.mL-1	PMID[543731]

☑ 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 NPC253987 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	383
0.1-0.2	3050
0.2-0.3	21061
0.3-0.4	11849
0.4-0.5	2528
0.5-0.6	2777
0.6-0.7	948
0.7-0.8	84
0.8-0.85	9
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9604	High Similarity	NPC19170
0.9463	High Similarity	NPC297862
0.9034	High Similarity	NPC312942
0.9034	High Similarity	NPC327095
0.899	High Similarity	NPC40455
0.8744	High Similarity	NPC470731
0.872	High Similarity	NPC476817
0.8476	Intermediate Similarity	NPC470732
0.8402	Intermediate Similarity	NPC63279
0.8364	Intermediate Similarity	NPC297642
0.8311	Intermediate Similarity	NPC475969
0.8311	Intermediate Similarity	NPC475859
0.8273	Intermediate Similarity	NPC165743
0.8265	Intermediate Similarity	NPC477175
0.8265	Intermediate Similarity	NPC470730
0.8063	Intermediate Similarity	NPC477177
0.8063	Intermediate Similarity	NPC474877
0.8018	Intermediate Similarity	NPC470729
0.8018	Intermediate Similarity	NPC477176
0.774	Intermediate Similarity	NPC294693
0.7593	Intermediate Similarity	NPC54420
0.7523	Intermediate Similarity	NPC162860
0.7364	Intermediate Similarity	NPC478158
0.7348	Intermediate Similarity	NPC56109
0.7348	Intermediate Similarity	NPC191382
0.7346	Intermediate Similarity	NPC473763
0.7346	Intermediate Similarity	NPC117244
0.7342	Intermediate Similarity	NPC31385
0.7342	Intermediate Similarity	NPC75726
0.7342	Intermediate Similarity	NPC110602
0.7319	Intermediate Similarity	NPC478029
0.7302	Intermediate Similarity	NPC171317
0.7285	Intermediate Similarity	NPC107077
0.7285	Intermediate Similarity	NPC223791
0.7281	Intermediate Similarity	NPC155444
0.7281	Intermediate Similarity	NPC31097
0.7277	Intermediate Similarity	NPC478157
0.7257	Intermediate Similarity	NPC281049
0.724	Intermediate Similarity	NPC470491
0.7237	Intermediate Similarity	NPC474896
0.7234	Intermediate Similarity	NPC478028
0.723	Intermediate Similarity	NPC471386
0.7228	Intermediate Similarity	NPC56233
0.7222	Intermediate Similarity	NPC220852
0.7222	Intermediate Similarity	NPC473640
0.7217	Intermediate Similarity	NPC128582
0.7203	Intermediate Similarity	NPC285343
0.7202	Intermediate Similarity	NPC475506
0.7188	Intermediate Similarity	NPC75634
0.7181	Intermediate Similarity	NPC477714
0.717	Intermediate Similarity	NPC255909
0.7169	Intermediate Similarity	NPC155143
0.716	Intermediate Similarity	NPC14812
0.7156	Intermediate Similarity	NPC94752
0.7156	Intermediate Similarity	NPC54744
0.7137	Intermediate Similarity	NPC477715
0.7136	Intermediate Similarity	NPC469938
0.7123	Intermediate Similarity	NPC17059
0.7118	Intermediate Similarity	NPC272174
0.7115	Intermediate Similarity	NPC11126
0.7104	Intermediate Similarity	NPC214827
0.7104	Intermediate Similarity	NPC473376
0.7104	Intermediate Similarity	NPC314930
0.7091	Intermediate Similarity	NPC182507
0.7087	Intermediate Similarity	NPC161861
0.7081	Intermediate Similarity	NPC24864
0.7073	Intermediate Similarity	NPC91895
0.7062	Intermediate Similarity	NPC228835
0.7032	Intermediate Similarity	NPC313421
0.7032	Intermediate Similarity	NPC100321
0.7028	Intermediate Similarity	NPC99939
0.7028	Intermediate Similarity	NPC308931
0.7026	Intermediate Similarity	NPC64216
0.7021	Intermediate Similarity	NPC69843
0.7009	Intermediate Similarity	NPC475024
0.7009	Intermediate Similarity	NPC213629
0.6995	Remote Similarity	NPC194881
0.6995	Remote Similarity	NPC17273
0.6995	Remote Similarity	NPC135601
0.6995	Remote Similarity	NPC141612
0.6991	Remote Similarity	NPC320968
0.6986	Remote Similarity	NPC64436
0.6965	Remote Similarity	NPC314176
0.6962	Remote Similarity	NPC89987
0.6952	Remote Similarity	NPC248462
0.6934	Remote Similarity	NPC143533
0.6926	Remote Similarity	NPC478011
0.6926	Remote Similarity	NPC478012
0.6919	Remote Similarity	NPC15840
0.6917	Remote Similarity	NPC28945
0.6917	Remote Similarity	NPC125181
0.6917	Remote Similarity	NPC242872
0.6917	Remote Similarity	NPC263117
0.6917	Remote Similarity	NPC314056
0.6916	Remote Similarity	NPC478077
0.6878	Remote Similarity	NPC293917
0.6864	Remote Similarity	NPC475258
0.6864	Remote Similarity	NPC476491
0.6858	Remote Similarity	NPC475259
0.6858	Remote Similarity	NPC471950
0.6858	Remote Similarity	NPC471945
0.6852	Remote Similarity	NPC103119
0.684	Remote Similarity	NPC91179
0.684	Remote Similarity	NPC16659
0.6836	Remote Similarity	NPC478013
0.6833	Remote Similarity	NPC149708
0.683	Remote Similarity	NPC477179
0.683	Remote Similarity	NPC317701
0.6828	Remote Similarity	NPC471946
0.6828	Remote Similarity	NPC471951
0.6825	Remote Similarity	NPC157583
0.6822	Remote Similarity	NPC472119
0.6806	Remote Similarity	NPC472323
0.68	Remote Similarity	NPC477181
0.68	Remote Similarity	NPC254850
0.68	Remote Similarity	NPC477178
0.68	Remote Similarity	NPC477180
0.6796	Remote Similarity	NPC478182
0.6792	Remote Similarity	NPC265710
0.6792	Remote Similarity	NPC12649
0.6791	Remote Similarity	NPC79062
0.6791	Remote Similarity	NPC472107
0.6787	Remote Similarity	NPC153400
0.6786	Remote Similarity	NPC476874
0.6773	Remote Similarity	NPC57994
0.6773	Remote Similarity	NPC289299
0.677	Remote Similarity	NPC470490
0.677	Remote Similarity	NPC477173
0.677	Remote Similarity	NPC477174
0.6763	Remote Similarity	NPC325976
0.676	Remote Similarity	NPC314882
0.6751	Remote Similarity	NPC909
0.6751	Remote Similarity	NPC475338
0.6745	Remote Similarity	NPC473380
0.6745	Remote Similarity	NPC240088
0.6744	Remote Similarity	NPC470003
0.674	Remote Similarity	NPC323927
0.674	Remote Similarity	NPC470488
0.6738	Remote Similarity	NPC473310
0.6731	Remote Similarity	NPC321939
0.6731	Remote Similarity	NPC114637
0.6727	Remote Similarity	NPC304203
0.6725	Remote Similarity	NPC191817
0.6725	Remote Similarity	NPC475359
0.6724	Remote Similarity	NPC471192
0.6723	Remote Similarity	NPC186351
0.6712	Remote Similarity	NPC476460
0.6711	Remote Similarity	NPC328596
0.6711	Remote Similarity	NPC328318
0.671	Remote Similarity	NPC317752
0.6709	Remote Similarity	NPC474196
0.6698	Remote Similarity	NPC163055
0.6697	Remote Similarity	NPC175474
0.6697	Remote Similarity	NPC321708
0.6696	Remote Similarity	NPC317373
0.6695	Remote Similarity	NPC238945
0.6695	Remote Similarity	NPC79386
0.6693	Remote Similarity	NPC315467
0.6683	Remote Similarity	NPC40070
0.6682	Remote Similarity	NPC474389
0.668	Remote Similarity	NPC477516
0.6667	Remote Similarity	NPC153980
0.6667	Remote Similarity	NPC318299
0.6667	Remote Similarity	NPC14325
0.6667	Remote Similarity	NPC471194
0.6667	Remote Similarity	NPC326363
0.6667	Remote Similarity	NPC6865
0.6667	Remote Similarity	NPC28848
0.6667	Remote Similarity	NPC472116
0.6667	Remote Similarity	NPC471193
0.6667	Remote Similarity	NPC258480
0.6654	Remote Similarity	NPC478006
0.6652	Remote Similarity	NPC327592
0.665	Remote Similarity	NPC293487
0.6638	Remote Similarity	NPC313804
0.6638	Remote Similarity	NPC315804
0.6637	Remote Similarity	NPC193761
0.6636	Remote Similarity	NPC129909
0.6636	Remote Similarity	NPC133003
0.6635	Remote Similarity	NPC478184
0.6629	Remote Similarity	NPC477633
0.6625	Remote Similarity	NPC33949
0.6623	Remote Similarity	NPC238457
0.6623	Remote Similarity	NPC72956
0.6622	Remote Similarity	NPC106235
0.6622	Remote Similarity	NPC239660
0.662	Remote Similarity	NPC470205
0.6612	Remote Similarity	NPC474183
0.6611	Remote Similarity	NPC319232
0.6611	Remote Similarity	NPC24370
0.661	Remote Similarity	NPC474195
0.6607	Remote Similarity	NPC212213
0.6607	Remote Similarity	NPC52557
0.6606	Remote Similarity	NPC66210
0.6604	Remote Similarity	NPC477976
0.6604	Remote Similarity	NPC242269
0.6602	Remote Similarity	NPC478009
0.6602	Remote Similarity	NPC478010
0.6596	Remote Similarity	NPC475736
0.659	Remote Similarity	NPC477003

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 NPC253987 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	586
0.2-0.3	1087
0.3-0.4	2249
0.4-0.5	2159
0.5-0.6	2206
0.6-0.7	619
0.7-0.8	33
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
0.7713	Intermediate Similarity	NPD7661	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7195	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD7944	Discontinued
0.7444	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD7619	Phase 3
0.7406	Intermediate Similarity	NPD7618	Phase 3
0.7371	Intermediate Similarity	NPD7789	Approved
0.7371	Intermediate Similarity	NPD7791	Approved
0.7371	Intermediate Similarity	NPD7952	Approved
0.7371	Intermediate Similarity	NPD7790	Approved
0.7371	Intermediate Similarity	NPD7953	Approved
0.7371	Intermediate Similarity	NPD7951	Approved
0.7371	Intermediate Similarity	NPD7950	Approved
0.7348	Intermediate Similarity	NPD7781	Approved
0.7348	Intermediate Similarity	NPD7780	Approved
0.7318	Intermediate Similarity	NPD7666	Phase 3
0.7318	Intermediate Similarity	NPD7665	Phase 2
0.7304	Intermediate Similarity	NPD7731	Approved
0.7304	Intermediate Similarity	NPD7730	Approved
0.7277	Intermediate Similarity	NPD7970	Approved
0.7277	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD8272	Phase 2
0.7241	Intermediate Similarity	NPD7824	Approved
0.7217	Intermediate Similarity	NPD7271	Approved
0.7175	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6269	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6268	Phase 1
0.7149	Intermediate Similarity	NPD7001	Phase 3
0.7143	Intermediate Similarity	NPD7483	Phase 2
0.7143	Intermediate Similarity	NPD7482	Phase 2
0.713	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6044	Discontinued
0.7032	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6999	Discontinued
0.703	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8114	Approved
0.7027	Intermediate Similarity	NPD8169	Discontinued
0.7027	Intermediate Similarity	NPD8115	Approved
0.6991	Remote Similarity	NPD7470	Discontinued
0.6972	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7711	Discontinued
0.6966	Remote Similarity	NPD8289	Discontinued
0.6964	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.692	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5017	Discontinued
0.6892	Remote Similarity	NPD7817	Phase 1
0.6884	Remote Similarity	NPD7394	Phase 2
0.6878	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD8246	Approved
0.6867	Remote Similarity	NPD8247	Approved
0.6864	Remote Similarity	NPD6664	Approved
0.6858	Remote Similarity	NPD6520	Phase 3
0.6858	Remote Similarity	NPD6521	Phase 3
0.6857	Remote Similarity	NPD8375	Approved
0.6856	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD2849	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8257	Approved
0.684	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.684	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8256	Approved
0.6837	Remote Similarity	NPD5809	Phase 3
0.6833	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.683	Remote Similarity	NPD8072	Approved
0.6829	Remote Similarity	NPD8250	Phase 2
0.6826	Remote Similarity	NPD8242	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7564	Discontinued
0.6814	Remote Similarity	NPD8322	Phase 2
0.6814	Remote Similarity	NPD5864	Phase 2
0.6806	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD2880	Discontinued
0.6784	Remote Similarity	NPD2442	Approved
0.6784	Remote Similarity	NPD2443	Approved
0.6781	Remote Similarity	NPD5198	Approved
0.6781	Remote Similarity	NPD5199	Approved
0.678	Remote Similarity	NPD2511	Approved
0.6774	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD4602	Approved
0.6773	Remote Similarity	NPD8484	Phase 2
0.677	Remote Similarity	NPD5489	Phase 1
0.677	Remote Similarity	NPD5491	Phase 3
0.6766	Remote Similarity	NPD8356	Approved
0.6763	Remote Similarity	NPD2720	Phase 1
0.6763	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD3430	Approved
0.6758	Remote Similarity	NPD3431	Approved
0.6752	Remote Similarity	NPD5884	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6771	Discontinued
0.6741	Remote Similarity	NPD7727	Phase 2
0.674	Remote Similarity	NPD3905	Phase 3
0.6738	Remote Similarity	NPD6470	Phase 3
0.6737	Remote Similarity	NPD7717	Approved
0.6737	Remote Similarity	NPD7716	Approved
0.6728	Remote Similarity	NPD3961	Discontinued
0.6727	Remote Similarity	NPD2717	Phase 2
0.6726	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5426	Phase 3
0.6725	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6164	Phase 2
0.6723	Remote Similarity	NPD6165	Phase 2
0.6723	Remote Similarity	NPD8430	Approved
0.6713	Remote Similarity	NPD5555	Phase 1
0.6712	Remote Similarity	NPD7434	Approved
0.6712	Remote Similarity	NPD6206	Phase 1
0.6711	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD8073	Approved
0.671	Remote Similarity	NPD8094	Discontinued
0.6708	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4639	Approved
0.6699	Remote Similarity	NPD4638	Approved
0.6699	Remote Similarity	NPD5862	Discovery
0.6699	Remote Similarity	NPD4640	Approved
0.6698	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4334	Discontinued
0.6696	Remote Similarity	NPD7568	Phase 1
0.6695	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4326	Phase 2
0.6682	Remote Similarity	NPD5508	Phase 1
0.6682	Remote Similarity	NPD5505	Discontinued
0.6682	Remote Similarity	NPD4615	Phase 2
0.6682	Remote Similarity	NPD7026	Phase 2
0.6681	Remote Similarity	NPD6888	Discontinued
0.6681	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD5487	Phase 1
0.6667	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7111	Discontinued
0.6667	Remote Similarity	NPD8093	Discontinued
0.6667	Remote Similarity	NPD7027	Phase 3
0.6667	Remote Similarity	NPD4415	Approved
0.6667	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5315	Discontinued
0.6653	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD2405	Phase 3
0.6651	Remote Similarity	NPD5636	Discontinued
0.6651	Remote Similarity	NPD8408	Discontinued
0.6641	Remote Similarity	NPD5461	Discontinued
0.6638	Remote Similarity	NPD4959	Approved
0.6638	Remote Similarity	NPD2357	Approved
0.6638	Remote Similarity	NPD4960	Approved
0.6637	Remote Similarity	NPD2881	Approved
0.6637	Remote Similarity	NPD2879	Approved
0.6636	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6626	Approved
0.6636	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7887	Approved
0.6625	Remote Similarity	NPD7888	Approved
0.6622	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5104	Approved
0.6619	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7469	Discontinued
0.6611	Remote Similarity	NPD7603	Discontinued
0.6609	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD2408	Discontinued
0.6605	Remote Similarity	NPD6595	Phase 3
0.6604	Remote Similarity	NPD750	Phase 2
0.6603	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6986	Phase 1
0.6597	Remote Similarity	NPD6173	Approved
0.6596	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD4852	Phase 2
0.659	Remote Similarity	NPD4957	Phase 2
0.6589	Remote Similarity	NPD8122	Approved
0.6589	Remote Similarity	NPD8123	Approved
0.6586	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4547	Phase 3
0.658	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD8020	Approved
0.6575	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD8021	Approved
0.6574	Remote Similarity	NPD8101	Phase 3
0.657	Remote Similarity	NPD8317	Phase 2
0.657	Remote Similarity	NPD8316	Phase 2
0.6569	Remote Similarity	NPD5986	Approved
0.6569	Remote Similarity	NPD5987	Approved
0.6568	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD5679	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6787	Phase 2
0.6565	Remote Similarity	NPD8260	Approved
0.6564	Remote Similarity	NPD3015	Discontinued
0.6562	Remote Similarity	NPD6224	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1658	Discontinued
0.6557	Remote Similarity	NPD6970	Phase 2
0.6557	Remote Similarity	NPD8159	Discontinued
0.6552	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7289	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