NPASS Compound

Structure

CID299035 OpenBabel06191716102D 67 70 0 0 1 0 0 0 0 0999 V2000 -3.0843 3.7815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3272 1.1366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9535 -4.0217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7448 -2.3022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9082 2.9562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3418 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7485 -6.2994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3129 -1.6507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1513 -1.6233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9317 -3.6600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5198 1.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5971 -1.2077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9619 -0.7960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1445 -1.5201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5360 -0.5828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5287 -0.4623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5470 -4.7006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5397 -4.5800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6302 2.7152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5383 2.7152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5971 2.2077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3418 0.8955 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 -2.8113 -1.2423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7245 -0.6231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1331 -5.2589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0843 2.7815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9352 0.2166 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9462 -3.9011 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.7375 -2.1817 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5714 2.2077 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3491 0.2250 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1445 2.5201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5383 -1.7152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2067 -0.7960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1294 -1.2617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0240 2.5201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2175 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9425 0.0961 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3491 0.7750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6302 -1.7152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9619 1.7960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3382 -2.9811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2067 1.7960 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0240 -1.5201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6084 3.4459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1429 2.6007 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0843 -1.7815 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5714 -1.2077 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -12.1404 -5.3795 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -13.7339 -6.0584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1221 -1.1412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5593 3.4056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7848 2.3641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0731 4.3313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1525 -0.6636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5506 -0.8239 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3309 -2.8606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3837 2.3641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3573 -1.2423 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 -2.1332 -0.9852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6092 3.4056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2175 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7 53 1 0 0 0 0 8 59 1 0 0 0 0 9 60 1 0 0 0 0 10 61 1 0 0 0 0 11 62 1 0 0 0 0 12 13 1 0 0 0 0 12 14 2 0 0 0 0 13 39 1 0 0 0 0 14 42 1 0 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 37 1 0 0 0 0 17 18 2 0 0 0 0 17 29 1 0 0 0 0 18 53 1 0 0 0 0 19 27 1 0 0 0 0 19 33 1 0 0 0 0 20 27 1 0 0 0 0 20 38 1 0 0 0 0 21 33 1 0 0 0 0 21 43 1 0 0 0 0 23 34 2 0 0 0 0 23 64 1 0 0 0 0 24 35 2 0 0 0 0 24 63 1 0 0 0 0 25 36 2 0 0 0 0 25 65 1 0 0 0 0 26 53 1 0 0 0 0 26 54 2 0 0 0 0 27 1 1 6 0 0 0 28 2 1 6 0 0 0 28 40 1 0 0 0 0 29 3 1 6 0 0 0 29 44 1 0 0 0 0 30 4 1 6 0 0 0 30 37 1 0 0 0 0 30 44 1 0 0 0 0 31 5 1 6 0 0 0 31 38 1 0 0 0 0 31 45 1 0 0 0 0 32 6 1 1 0 0 0 32 39 1 0 0 0 0 32 41 1 0 0 0 0 33 66 1 1 0 0 0 34 45 1 0 0 0 0 34 51 1 0 0 0 0 35 46 1 0 0 0 0 35 50 1 0 0 0 0 36 47 1 0 0 0 0 36 52 1 0 0 0 0 37 55 2 0 0 0 0 38 56 1 6 0 0 0 39 59 1 6 0 0 0 40 22 1 6 0 0 0 40 60 1 0 0 0 0 41 22 1 6 0 0 0 41 67 1 0 0 0 0 42 50 2 0 0 0 0 42 63 1 0 0 0 0 43 57 2 0 0 0 0 43 67 1 0 0 0 0 44 61 1 1 0 0 0 45 62 1 1 0 0 0 46 52 2 0 0 0 0 46 65 1 0 0 0 0 47 51 2 0 0 0 0 47 64 1 0 0 0 0 48 49 2 0 0 0 0 48 58 1 0 0 0 0 48 66 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	941.5
Volume:	950.947
LogP:	4.432
LogD:	4.977
LogS:	-4.566
# Rotatable Bonds:	18
TPSA:	251.24
# H-Bond Aceptor:	19
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.1
Synthetic Accessibility Score:	5.876
Fsp3:	0.646
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.797
MDCK Permeability:	2.691489498829469e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.196
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	73.9234619140625%
Volume Distribution (VD):	4.221
Pgp-substrate:	13.525480270385742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.492
CYP3A4-substrate:	0.301

ADMET: Excretion

Clearance (CL):	8.972
Half-life (T1/2):	0.063

ADMET: Toxicity

hERG Blockers:	0.701
Human Hepatotoxicity (H-HT):	0.883
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.984
Maximum Recommended Daily Dose:	0.901
Skin Sensitization:	0.045
Carcinogencity:	0.37
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.329

Download Data

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

Natural Product: NPC299035

Natural Product ID:	NPC299035
*Common Name:**	Kabiramide C
IUPAC Name:	n.a.
Synonyms:	Kabiramide C
Standard InCHIKey:	VDALFVIVHBKWES-NODZMMCWSA-N
Standard InCHI:	InChI=1S/C48H71N5O14/c1-27-19-33(66-48(49)58)21-43(57)67-41(22-40(60-9)28(2)15-16-37(55)30(4)44(61-10)29(3)17-18-53(7)26-54)32(6)39(59-8)13-12-14-42-50-35(24-63-42)46-52-36(25-65-46)47-51-34(23-64-47)45(62-11)31(5)38(56)20-27/h12,14,17-18,23-33,38-41,44-45,56H,13,15-16,19-22H2,1-11H3,(H2,49,58)/b14-12+,18-17+/t27-,28-,29+,30-,31-,32+,33-,38-,39-,40-,41-,44+,45+/m0/s1
SMILES:	C[C@H]1C[C@@H](CC(=O)O[C@@H](C[C@@H]([C@@H](C)CCC(=O)[C@H](C)[C@@H]([C@H](C)/C=C/N(C)C=O)OC)OC)[C@H](C)[C@H](C/C=C/c2nc(-c3nc(-c4nc(co4)[C@@H]([C@@H](C)[C@H](C1)O)OC)co3)co2)OC)OC(=N)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443430
PubChem CID:	44593597
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO10690	Hexabranchus sanguineus	Species	Hexabranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19254038]
NPO29155	Pachastrissa nux	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21410162]
NPO10690	Hexabranchus sanguineus	Species	Hexabranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28098996]
NPO7298.1	Brassica napus subsp. rapifera	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29155	Pachastrissa nux	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29306	Colchicum szovitsii	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10690	Hexabranchus sanguineus	Species	Hexabranchidae	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	6
MIC	3

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.3	ug.mL-1	PMID[573226]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.8	ug.mL-1	PMID[573226]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	470.0	nM	PMID[573229]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.3	ug.mL-1	PMID[573226]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	0.016	ug.mL-1	PMID[573228]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	0.25	ug.mL-1	PMID[573228]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	0.125	ug.mL-1	PMID[573228]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	4790.0	nM	PMID[573229]
NPT27	Others	Unspecified		IC50	=	7590.0	nM	PMID[573229]

☑ 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 NPC299035 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	265
0.1-0.2	1578
0.2-0.3	8068
0.3-0.4	20788
0.4-0.5	10709
0.5-0.6	1196
0.6-0.7	54
0.7-0.8	8
0.8-0.85	0
0.85-0.9	5
0.9-0.95	18
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC177432
0.9951	High Similarity	NPC477218
0.9951	High Similarity	NPC168135
0.9951	High Similarity	NPC322800
0.9804	High Similarity	NPC37924
0.9756	High Similarity	NPC325683
0.9755	High Similarity	NPC477219
0.9565	High Similarity	NPC476828
0.942	High Similarity	NPC476827
0.942	High Similarity	NPC476831
0.942	High Similarity	NPC476826
0.9375	High Similarity	NPC476830
0.9014	High Similarity	NPC476832
0.8143	Intermediate Similarity	NPC476829
0.7282	Intermediate Similarity	NPC30527
0.7264	Intermediate Similarity	NPC58001
0.7264	Intermediate Similarity	NPC314523
0.7162	Intermediate Similarity	NPC208297
0.7162	Intermediate Similarity	NPC224395
0.7048	Intermediate Similarity	NPC258022
0.7008	Intermediate Similarity	NPC477585
0.7008	Intermediate Similarity	NPC477588
0.7008	Intermediate Similarity	NPC477590
0.7008	Intermediate Similarity	NPC477586
0.6964	Remote Similarity	NPC295653
0.6964	Remote Similarity	NPC107458
0.6937	Remote Similarity	NPC88938
0.6937	Remote Similarity	NPC58112
0.6937	Remote Similarity	NPC306300
0.6926	Remote Similarity	NPC477589
0.6926	Remote Similarity	NPC477587
0.6828	Remote Similarity	NPC289029
0.6828	Remote Similarity	NPC48323
0.6741	Remote Similarity	NPC199461
0.6741	Remote Similarity	NPC315411
0.6741	Remote Similarity	NPC103452
0.6741	Remote Similarity	NPC46313
0.6716	Remote Similarity	NPC196449
0.6716	Remote Similarity	NPC314222
0.6681	Remote Similarity	NPC309919
0.6681	Remote Similarity	NPC49195
0.6667	Remote Similarity	NPC472436
0.6569	Remote Similarity	NPC315061
0.655	Remote Similarity	NPC472435
0.6523	Remote Similarity	NPC165964
0.6509	Remote Similarity	NPC315872
0.6426	Remote Similarity	NPC102593
0.6426	Remote Similarity	NPC196718
0.6374	Remote Similarity	NPC258048
0.6326	Remote Similarity	NPC211555
0.6314	Remote Similarity	NPC148889
0.6304	Remote Similarity	NPC472434
0.6279	Remote Similarity	NPC186452
0.6268	Remote Similarity	NPC207620
0.6246	Remote Similarity	NPC169716
0.6245	Remote Similarity	NPC182222
0.6239	Remote Similarity	NPC12660
0.6216	Remote Similarity	NPC72715
0.621	Remote Similarity	NPC54983
0.621	Remote Similarity	NPC314633
0.6202	Remote Similarity	NPC316224
0.6192	Remote Similarity	NPC161801
0.6148	Remote Similarity	NPC477979
0.6148	Remote Similarity	NPC471979
0.6134	Remote Similarity	NPC152620
0.609	Remote Similarity	NPC53534
0.6048	Remote Similarity	NPC313804
0.6048	Remote Similarity	NPC315804
0.6038	Remote Similarity	NPC124300
0.6037	Remote Similarity	NPC471978
0.6034	Remote Similarity	NPC220408
0.6031	Remote Similarity	NPC310618
0.6031	Remote Similarity	NPC58209
0.6023	Remote Similarity	NPC26543
0.6023	Remote Similarity	NPC10904
0.6022	Remote Similarity	NPC473833
0.6015	Remote Similarity	NPC291609
0.6008	Remote Similarity	NPC140296
0.5992	Remote Similarity	NPC97746
0.5984	Remote Similarity	NPC194740
0.5978	Remote Similarity	NPC328928
0.5973	Remote Similarity	NPC475455
0.5969	Remote Similarity	NPC57453
0.5955	Remote Similarity	NPC471015
0.5954	Remote Similarity	NPC208364
0.5953	Remote Similarity	NPC141053
0.5952	Remote Similarity	NPC205372
0.5948	Remote Similarity	NPC476514
0.5945	Remote Similarity	NPC186351
0.5944	Remote Similarity	NPC131885
0.594	Remote Similarity	NPC473800
0.594	Remote Similarity	NPC67401
0.5933	Remote Similarity	NPC326930
0.5933	Remote Similarity	NPC475301
0.5929	Remote Similarity	NPC212766
0.5929	Remote Similarity	NPC289423
0.5926	Remote Similarity	NPC316403
0.5925	Remote Similarity	NPC63971
0.5925	Remote Similarity	NPC91868
0.592	Remote Similarity	NPC298436
0.5918	Remote Similarity	NPC269367
0.5912	Remote Similarity	NPC470042
0.5911	Remote Similarity	NPC13603
0.5904	Remote Similarity	NPC312645
0.5891	Remote Similarity	NPC220852
0.5887	Remote Similarity	NPC153452
0.5885	Remote Similarity	NPC184680
0.5885	Remote Similarity	NPC240384
0.5882	Remote Similarity	NPC244536
0.5875	Remote Similarity	NPC260434
0.5874	Remote Similarity	NPC53255
0.5874	Remote Similarity	NPC85879
0.5871	Remote Similarity	NPC180668
0.5871	Remote Similarity	NPC148896
0.5871	Remote Similarity	NPC471013
0.5865	Remote Similarity	NPC173250
0.5863	Remote Similarity	NPC313966
0.5863	Remote Similarity	NPC314254
0.5862	Remote Similarity	NPC470784
0.5862	Remote Similarity	NPC470785
0.5861	Remote Similarity	NPC230683
0.5861	Remote Similarity	NPC209981
0.5856	Remote Similarity	NPC166712
0.5852	Remote Similarity	NPC120513
0.584	Remote Similarity	NPC168922
0.5836	Remote Similarity	NPC329982
0.5833	Remote Similarity	NPC323969
0.5833	Remote Similarity	NPC75179
0.5833	Remote Similarity	NPC160100
0.5833	Remote Similarity	NPC188400
0.583	Remote Similarity	NPC284888
0.5827	Remote Similarity	NPC1608
0.5824	Remote Similarity	NPC285343
0.5823	Remote Similarity	NPC16066
0.5821	Remote Similarity	NPC315893
0.5821	Remote Similarity	NPC313587
0.5821	Remote Similarity	NPC181081
0.5821	Remote Similarity	NPC316110
0.5817	Remote Similarity	NPC281049
0.5817	Remote Similarity	NPC99891
0.5814	Remote Similarity	NPC14288
0.581	Remote Similarity	NPC90019
0.5808	Remote Similarity	NPC34770
0.5802	Remote Similarity	NPC474183
0.5802	Remote Similarity	NPC101350
0.58	Remote Similarity	NPC85702
0.5792	Remote Similarity	NPC321592
0.5792	Remote Similarity	NPC54803
0.5791	Remote Similarity	NPC101312
0.5791	Remote Similarity	NPC473639
0.5789	Remote Similarity	NPC123839
0.5788	Remote Similarity	NPC185197
0.5787	Remote Similarity	NPC478141
0.5784	Remote Similarity	NPC203373
0.5783	Remote Similarity	NPC89508
0.5781	Remote Similarity	NPC319232
0.5781	Remote Similarity	NPC24370
0.578	Remote Similarity	NPC172355
0.5779	Remote Similarity	NPC216507
0.5775	Remote Similarity	NPC223409
0.5775	Remote Similarity	NPC322135
0.5768	Remote Similarity	NPC475315
0.5768	Remote Similarity	NPC18487
0.5768	Remote Similarity	NPC187558
0.5768	Remote Similarity	NPC324619
0.5766	Remote Similarity	NPC215837
0.5766	Remote Similarity	NPC146418
0.5765	Remote Similarity	NPC475271
0.5763	Remote Similarity	NPC28945
0.5763	Remote Similarity	NPC15801
0.5763	Remote Similarity	NPC235685
0.5762	Remote Similarity	NPC476515
0.5761	Remote Similarity	NPC100734
0.5761	Remote Similarity	NPC315634
0.5761	Remote Similarity	NPC88923
0.5754	Remote Similarity	NPC314270
0.5754	Remote Similarity	NPC303658
0.5749	Remote Similarity	NPC478158
0.5747	Remote Similarity	NPC475619
0.574	Remote Similarity	NPC227824
0.5738	Remote Similarity	NPC317572
0.5736	Remote Similarity	NPC100547
0.5736	Remote Similarity	NPC33949
0.573	Remote Similarity	NPC191489
0.573	Remote Similarity	NPC475533
0.5726	Remote Similarity	NPC314834
0.572	Remote Similarity	NPC475816
0.572	Remote Similarity	NPC314882
0.5719	Remote Similarity	NPC260909
0.5714	Remote Similarity	NPC95240
0.571	Remote Similarity	NPC115282
0.5709	Remote Similarity	NPC266249
0.5709	Remote Similarity	NPC287208
0.5709	Remote Similarity	NPC323752
0.5709	Remote Similarity	NPC282346
0.5704	Remote Similarity	NPC14812
0.5698	Remote Similarity	NPC124920
0.5698	Remote Similarity	NPC118559
0.5698	Remote Similarity	NPC261251
0.5698	Remote Similarity	NPC34580

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 NPC299035 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	516
0.2-0.3	1640
0.3-0.4	3605
0.4-0.5	2827
0.5-0.6	384
0.6-0.7	13
0.7-0.8	1
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
0.6933	Remote Similarity	NPD7896	Approved
0.6509	Remote Similarity	NPD6444	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7853	Phase 2
0.6463	Remote Similarity	NPD6347	Phase 2
0.6452	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD8370	Discontinued
0.6446	Remote Similarity	NPD6974	Phase 3
0.6364	Remote Similarity	NPD7490	Discontinued
0.6341	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.626	Remote Similarity	NPD4368	Phase 2
0.623	Remote Similarity	NPD7031	Phase 1
0.6189	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.616	Remote Similarity	NPD3263	Phase 3
0.6154	Remote Similarity	NPD7180	Phase 3
0.6151	Remote Similarity	NPD8255	Phase 2
0.6143	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5532	Phase 2
0.6118	Remote Similarity	NPD2951	Discontinued
0.6107	Remote Similarity	NPD3945	Discontinued
0.6107	Remote Similarity	NPD8324	Phase 2
0.61	Remote Similarity	NPD8116	Phase 3
0.61	Remote Similarity	NPD8117	Approved
0.6092	Remote Similarity	NPD2779	Approved
0.6045	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD3006	Discontinued
0.6024	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD5924	Discontinued
0.6024	Remote Similarity	NPD8374	Phase 3
0.6023	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD5482	Discontinued
0.6008	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5922	Phase 3
0.5992	Remote Similarity	NPD8329	Phase 3
0.5985	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD7022	Phase 2
0.5976	Remote Similarity	NPD8356	Approved
0.5976	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.597	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.597	Remote Similarity	NPD8375	Approved
0.5966	Remote Similarity	NPD2778	Approved
0.5962	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5908	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.596	Remote Similarity	NPD8479	Phase 2
0.5955	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.5953	Remote Similarity	NPD4373	Phase 2
0.5951	Remote Similarity	NPD5293	Phase 2
0.5949	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.5945	Remote Similarity	NPD8430	Approved
0.5945	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.5925	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD3392	Approved
0.5906	Remote Similarity	NPD5640	Discontinued
0.5904	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.5898	Remote Similarity	NPD4952	Phase 3
0.5896	Remote Similarity	NPD5850	Phase 3
0.5894	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD6169	Phase 1
0.5885	Remote Similarity	NPD3507	Phase 2
0.5882	Remote Similarity	NPD4086	Phase 1
0.5871	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.587	Remote Similarity	NPD5866	Approved
0.5863	Remote Similarity	NPD8160	Phase 2
0.5863	Remote Similarity	NPD7053	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD8104	Phase 3
0.5836	Remote Similarity	NPD8421	Discontinued
0.5836	Remote Similarity	NPD8463	Approved
0.5833	Remote Similarity	NPD6857	Phase 3
0.5823	Remote Similarity	NPD1638	Discovery
0.582	Remote Similarity	NPD7994	Phase 2
0.5818	Remote Similarity	NPD5450	Discontinued
0.5817	Remote Similarity	NPD7417	Discontinued
0.5817	Remote Similarity	NPD7878	Phase 2
0.5815	Remote Similarity	NPD8247	Approved
0.5815	Remote Similarity	NPD8246	Approved
0.5814	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD1867	Approved
0.5808	Remote Similarity	NPD3074	Discontinued
0.5792	Remote Similarity	NPD772	Phase 3
0.5779	Remote Similarity	NPD7885	Phase 2
0.5779	Remote Similarity	NPD7886	Phase 2
0.5777	Remote Similarity	NPD8325	Phase 3
0.5777	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.5777	Remote Similarity	NPD8326	Phase 3
0.5775	Remote Similarity	NPD5479	Discontinued
0.5775	Remote Similarity	NPD1659	Phase 1
0.5766	Remote Similarity	NPD5416	Discontinued
0.5766	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD7803	Approved
0.5753	Remote Similarity	NPD1505	Phase 2
0.5749	Remote Similarity	NPD1955	Discontinued
0.574	Remote Similarity	NPD6023	Discontinued
0.5736	Remote Similarity	NPD6716	Phase 1
0.5732	Remote Similarity	NPD4392	Phase 2
0.573	Remote Similarity	NPD7708	Approved
0.572	Remote Similarity	NPD8289	Discontinued
0.572	Remote Similarity	NPD1480	Clinical (unspecified phase)
0.5719	Remote Similarity	NPD8459	Approved
0.5719	Remote Similarity	NPD8460	Approved
0.5714	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD7470	Discontinued
0.5697	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.5693	Remote Similarity	NPD7955	Approved
0.5693	Remote Similarity	NPD7956	Approved
0.5692	Remote Similarity	NPD5632	Approved
0.5688	Remote Similarity	NPD4369	Phase 2
0.5683	Remote Similarity	NPD5857	Phase 3
0.568	Remote Similarity	NPD8097	Phase 3
0.568	Remote Similarity	NPD8096	Phase 3
0.567	Remote Similarity	NPD7797	Approved
0.567	Remote Similarity	NPD7796	Approved
0.5668	Remote Similarity	NPD8322	Phase 2
0.5663	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.5661	Remote Similarity	NPD7777	Approved
0.5661	Remote Similarity	NPD7778	Approved
0.5661	Remote Similarity	NPD8253	Phase 3
0.5661	Remote Similarity	NPD53	Approved
0.5654	Remote Similarity	NPD5022	Discontinued
0.5649	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.5637	Remote Similarity	NPD3259	Approved
0.5633	Remote Similarity	NPD6863	Phase 2
0.5632	Remote Similarity	NPD7688	Phase 1
0.5632	Remote Similarity	NPD5461	Discontinued
0.5632	Remote Similarity	NPD6962	Phase 2
0.563	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.5629	Remote Similarity	NPD8357	Approved
0.5618	Remote Similarity	NPD4322	Discontinued
0.5618	Remote Similarity	NPD7605	Discovery
0.5614	Remote Similarity	NPD6627	Discontinued
0.5613	Remote Similarity	NPD5817	Discontinued
0.5604	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.5602	Remote Similarity	NPD1927	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