NPASS Compound

Structure

NPC279871 OpenBabel07101718242D 69 72 0 0 1 0 0 0 0 0999 V2000 3.6093 7.8051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0998 -0.3357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2971 0.0724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0579 -1.4310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2594 4.2204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9711 4.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8291 1.2316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3185 -5.6345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5377 8.0955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9397 -1.2952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4880 -8.1906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5416 -7.2193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6200 -8.6299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2534 7.4366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7272 -6.6873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8056 -8.0978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8254 -2.6909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6679 -4.1500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6679 -2.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5104 -3.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0117 -3.8467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1682 -3.9806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1405 -4.6364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0448 -6.5944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2435 -0.8989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5436 4.8793 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7583 4.0081 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9361 0.2647 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8592 -7.1265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8254 -3.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5104 -2.6909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0287 -1.6363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6423 -4.4226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2980 -4.1500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0984 -5.6231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0407 6.4874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7470 -4.7236 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3755 -1.3381 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4740 3.3492 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9074 0.2111 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6152 4.5889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2152 -2.5911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6391 -3.2390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2613 2.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8087 -0.1550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9450 -5.1009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1491 -5.4104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7994 -0.5543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7564 5.8285 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5423 -0.7938 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0816 -3.5546 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6659 -2.2666 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4025 3.6396 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3329 2.1096 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6796 -4.9010 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0653 -5.5161 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8299 3.7177 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3528 -2.2045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1122 6.1970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7764 -4.6585 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8995 5.2477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1876 -2.5643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5939 -3.4255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9770 1.7411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3181 0.6738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4993 -5.9004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2169 -6.3117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4777 0.1430 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 9 1 0 0 0 0 2 10 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 8 55 1 0 0 0 0 9 14 1 0 0 0 0 10 32 2 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 14 36 1 0 0 0 0 15 29 2 0 0 0 0 16 29 1 0 0 0 0 17 19 1 0 0 0 0 17 30 2 0 0 0 0 18 20 2 0 0 0 0 18 30 1 0 0 0 0 19 31 2 0 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 22 37 1 0 0 0 0 23 30 1 0 0 0 0 24 29 1 0 0 0 0 26 5 1 1 0 0 0 26 41 1 0 0 0 0 26 49 1 0 0 0 0 27 6 1 6 0 0 0 27 39 1 0 0 0 0 27 57 1 0 0 0 0 28 7 1 6 0 0 0 28 40 1 0 0 0 0 28 69 1 0 0 0 0 31 58 1 0 0 0 0 32 42 1 0 0 0 0 32 50 1 0 0 0 0 33 21 1 1 0 0 0 33 46 1 0 0 0 0 33 51 1 0 0 0 0 34 23 1 1 0 0 0 34 43 1 0 0 0 0 34 55 1 0 0 0 0 35 24 1 1 0 0 0 35 47 1 0 0 0 0 35 56 1 0 0 0 0 36 49 2 3 0 0 0 36 59 1 0 0 0 0 37 56 1 0 0 0 0 37 60 1 6 0 0 0 38 25 1 1 0 0 0 38 48 1 0 0 0 0 38 52 1 0 0 0 0 39 44 1 6 0 0 0 39 53 1 0 0 0 0 40 45 1 0 0 0 0 40 54 1 6 0 0 0 41 53 2 3 0 0 0 41 61 1 0 0 0 0 42 51 2 3 0 0 0 42 62 1 0 0 0 0 43 52 2 3 0 0 0 43 63 1 0 0 0 0 44 54 2 3 0 0 0 44 64 1 0 0 0 0 45 50 2 3 0 0 0 45 65 1 0 0 0 0 46 56 1 0 0 0 0 46 66 2 0 0 0 0 47 55 1 0 0 0 0 47 67 2 0 0 0 0 48 68 2 0 0 0 0 48 69 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	962.47
Volume:	964.602
LogP:	0.662
LogD:	0.736
LogS:	-2.044
# Rotatable Bonds:	15
TPSA:	309.19
# H-Bond Aceptor:	21
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.059
Synthetic Accessibility Score:	7.056
Fsp3:	0.521
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:	-6.82
MDCK Permeability:	1.2447449989849702e-05
Pgp-inhibitor:	0.835
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.867
20% Bioavailability (F20%):	0.051
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.128
Plasma Protein Binding (PPB):	49.52392578125%
Volume Distribution (VD):	0.341
Pgp-substrate:	46.79718017578125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.334
CYP2D6-inhibitor:	0.094
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.022

ADMET: Excretion

Clearance (CL):	2.16
Half-life (T1/2):	0.9

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.992
Drug-inuced Liver Injury (DILI):	0.991
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.15
Maximum Recommended Daily Dose:	0.803
Skin Sensitization:	0.213
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.617

Download Data

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

Natural Product: NPC279871

Natural Product ID:	NPC279871
*Common Name:**	Molassamide
IUPAC Name:	(2S,3R)-N-[(2S,5S,8S,11R,12S,15Z,18S,21R)-2-benzyl-15-ethylidene-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]-2-[[(2S)-2-(butanoylamino)propanoyl]amino]-3-hydroxybutanamide
Synonyms:	Molassamide
Standard InCHIKey:	KXSGCAPYMUMVSH-VFYPFKDGSA-N
Standard InCHI:	InChI=1S/C48H66N8O13/c1-9-14-36(59)49-26(5)41(61)53-39(27(6)57)44(64)54-40-28(7)69-48(68)38(25(3)4)52-43(63)34(23-30-17-19-31(58)20-18-30)55(8)47(67)35(24-29-15-12-11-13-16-29)56-37(60)22-21-33(46(56)66)51-42(62)32(10-2)50-45(40)65/h10-13,15-20,25-28,33-35,37-40,57-58,60H,9,14,21-24H2,1-8H3,(H,49,59)(H,50,65)(H,51,62)(H,52,63)(H,53,61)(H,54,64)/b32-10-/t26-,27+,28+,33-,34-,35-,37+,38-,39-,40-/m0/s1
SMILES:	CCCC(=N[C@@H](C)C(=N[C@@H]([C@@H](C)O)C(=N[C@H]1[C@@H](C)OC(=O)[C@H](C(C)C)N=C([C@H](Cc2ccc(cc2)O)N(C)C(=O)[C@H](Cc2ccccc2)N2[C@@H](CC[C@@H](C2=O)N=C(/C(=C/C)/N=C1O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077010
PubChem CID:	45379965
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO4193	Dichothrix utahensis	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20020755]
NPO4193	Dichothrix utahensis	Species	Rivulariaceae	Bacteria	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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4417	Individual Protein	Elastase 1	Sus scrofa	IC50	=	32.0	nM	PMID[540126]
NPT2682	Individual Protein	Alpha-chymotrypsin	Bos taurus	IC50	=	234.0	nM	PMID[540126]

☑ 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 NPC279871 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	194
0.1-0.2	1011
0.2-0.3	4062
0.3-0.4	12715
0.4-0.5	11600
0.5-0.6	11669
0.6-0.7	1013
0.7-0.8	337
0.8-0.85	46
0.85-0.9	25
0.9-0.95	19
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9811	High Similarity	NPC269750
0.9811	High Similarity	NPC194671
0.9571	High Similarity	NPC294951
0.956	High Similarity	NPC306804
0.956	High Similarity	NPC137627
0.943	High Similarity	NPC107938
0.943	High Similarity	NPC294516
0.9379	High Similarity	NPC159767
0.9379	High Similarity	NPC155506
0.9375	High Similarity	NPC230611
0.9333	High Similarity	NPC471050
0.9333	High Similarity	NPC471048
0.9333	High Similarity	NPC471049
0.9313	High Similarity	NPC40234
0.9286	High Similarity	NPC163961
0.9286	High Similarity	NPC473305
0.9259	High Similarity	NPC476227
0.9259	High Similarity	NPC473402
0.9202	High Similarity	NPC50016
0.9198	High Similarity	NPC273755
0.9141	High Similarity	NPC473354
0.9091	High Similarity	NPC45037
0.9074	High Similarity	NPC475204
0.9074	High Similarity	NPC46009
0.9074	High Similarity	NPC475123
0.9024	High Similarity	NPC26108
0.8869	High Similarity	NPC476321
0.8837	High Similarity	NPC61332
0.8837	High Similarity	NPC240130
0.8817	High Similarity	NPC471526
0.8735	High Similarity	NPC248670
0.8686	High Similarity	NPC302715
0.8683	High Similarity	NPC158277
0.8647	High Similarity	NPC473404
0.8571	High Similarity	NPC471165
0.8537	High Similarity	NPC471053
0.8537	High Similarity	NPC471052
0.8537	High Similarity	NPC471051
0.8475	Intermediate Similarity	NPC65714
0.8466	Intermediate Similarity	NPC473378
0.8466	Intermediate Similarity	NPC473407
0.838	Intermediate Similarity	NPC473371
0.8373	Intermediate Similarity	NPC63931
0.8371	Intermediate Similarity	NPC328763
0.8352	Intermediate Similarity	NPC102959
0.8343	Intermediate Similarity	NPC89831
0.8333	Intermediate Similarity	NPC471592
0.8323	Intermediate Similarity	NPC233702
0.8305	Intermediate Similarity	NPC60516
0.8302	Intermediate Similarity	NPC16188
0.8274	Intermediate Similarity	NPC302597
0.8272	Intermediate Similarity	NPC262166
0.8272	Intermediate Similarity	NPC202198
0.8269	Intermediate Similarity	NPC239762
0.8269	Intermediate Similarity	NPC163392
0.8239	Intermediate Similarity	NPC81026
0.8187	Intermediate Similarity	NPC323662
0.8176	Intermediate Similarity	NPC266741
0.8176	Intermediate Similarity	NPC198254
0.8176	Intermediate Similarity	NPC274198
0.816	Intermediate Similarity	NPC473341
0.8148	Intermediate Similarity	NPC473491
0.811	Intermediate Similarity	NPC39431
0.8107	Intermediate Similarity	NPC61004
0.8092	Intermediate Similarity	NPC196243
0.8084	Intermediate Similarity	NPC469243
0.8079	Intermediate Similarity	NPC315542
0.807	Intermediate Similarity	NPC276506
0.8059	Intermediate Similarity	NPC141957
0.8056	Intermediate Similarity	NPC248822
0.8047	Intermediate Similarity	NPC472923
0.8047	Intermediate Similarity	NPC223207
0.8035	Intermediate Similarity	NPC136797
0.8024	Intermediate Similarity	NPC244336
0.8	Intermediate Similarity	NPC290755
0.8	Intermediate Similarity	NPC254700
0.8	Intermediate Similarity	NPC471771
0.8	Intermediate Similarity	NPC475421
0.8	Intermediate Similarity	NPC477551
0.8	Intermediate Similarity	NPC304074
0.7989	Intermediate Similarity	NPC477550
0.7989	Intermediate Similarity	NPC477552
0.7987	Intermediate Similarity	NPC476989
0.7976	Intermediate Similarity	NPC475544
0.7965	Intermediate Similarity	NPC196091
0.7953	Intermediate Similarity	NPC328649
0.7939	Intermediate Similarity	NPC5194
0.7939	Intermediate Similarity	NPC261934
0.7937	Intermediate Similarity	NPC91953
0.7929	Intermediate Similarity	NPC241794
0.7903	Intermediate Similarity	NPC469443
0.7901	Intermediate Similarity	NPC174122
0.7901	Intermediate Similarity	NPC64140
0.7889	Intermediate Similarity	NPC94862
0.7885	Intermediate Similarity	NPC257390
0.7875	Intermediate Similarity	NPC197921
0.787	Intermediate Similarity	NPC471527
0.7865	Intermediate Similarity	NPC470903
0.7865	Intermediate Similarity	NPC470112
0.7865	Intermediate Similarity	NPC167763
0.7845	Intermediate Similarity	NPC234069
0.7844	Intermediate Similarity	NPC244509
0.7844	Intermediate Similarity	NPC473580
0.7831	Intermediate Similarity	NPC56685
0.7831	Intermediate Similarity	NPC122590
0.7829	Intermediate Similarity	NPC477462
0.7826	Intermediate Similarity	NPC469360
0.7818	Intermediate Similarity	NPC475168
0.7818	Intermediate Similarity	NPC7817
0.7809	Intermediate Similarity	NPC477637
0.7778	Intermediate Similarity	NPC133470
0.7778	Intermediate Similarity	NPC191863
0.7778	Intermediate Similarity	NPC289776
0.7778	Intermediate Similarity	NPC299806
0.7772	Intermediate Similarity	NPC314083
0.7771	Intermediate Similarity	NPC475532
0.776	Intermediate Similarity	NPC477526
0.7759	Intermediate Similarity	NPC471568
0.7759	Intermediate Similarity	NPC473693
0.7753	Intermediate Similarity	NPC153554
0.7746	Intermediate Similarity	NPC473502
0.7738	Intermediate Similarity	NPC476268
0.7727	Intermediate Similarity	NPC165285
0.7727	Intermediate Similarity	NPC17698
0.7716	Intermediate Similarity	NPC161069
0.7714	Intermediate Similarity	NPC328494
0.7713	Intermediate Similarity	NPC473450
0.7708	Intermediate Similarity	NPC478005
0.7706	Intermediate Similarity	NPC287757
0.7706	Intermediate Similarity	NPC319320
0.7701	Intermediate Similarity	NPC186617
0.7701	Intermediate Similarity	NPC280022
0.7697	Intermediate Similarity	NPC9373
0.7692	Intermediate Similarity	NPC4910
0.7688	Intermediate Similarity	NPC6570
0.7688	Intermediate Similarity	NPC127741
0.768	Intermediate Similarity	NPC326333
0.768	Intermediate Similarity	NPC138083
0.7679	Intermediate Similarity	NPC470902
0.7669	Intermediate Similarity	NPC476978
0.7656	Intermediate Similarity	NPC220060
0.7654	Intermediate Similarity	NPC32064
0.7651	Intermediate Similarity	NPC2501
0.7644	Intermediate Similarity	NPC209463
0.764	Intermediate Similarity	NPC242159
0.764	Intermediate Similarity	NPC313694
0.7637	Intermediate Similarity	NPC276120
0.7634	Intermediate Similarity	NPC477638
0.7634	Intermediate Similarity	NPC59827
0.7634	Intermediate Similarity	NPC477632
0.7634	Intermediate Similarity	NPC184933
0.7627	Intermediate Similarity	NPC164608
0.7622	Intermediate Similarity	NPC209509
0.7617	Intermediate Similarity	NPC469444
0.761	Intermediate Similarity	NPC244866
0.7606	Intermediate Similarity	NPC50548
0.7602	Intermediate Similarity	NPC326027
0.7602	Intermediate Similarity	NPC1390
0.7602	Intermediate Similarity	NPC62104
0.76	Intermediate Similarity	NPC129486
0.7598	Intermediate Similarity	NPC119652
0.7598	Intermediate Similarity	NPC97526
0.7596	Intermediate Similarity	NPC329731
0.758	Intermediate Similarity	NPC296712
0.7576	Intermediate Similarity	NPC314358
0.7553	Intermediate Similarity	NPC144314
0.755	Intermediate Similarity	NPC478007
0.7544	Intermediate Similarity	NPC56635
0.753	Intermediate Similarity	NPC135121
0.753	Intermediate Similarity	NPC138775
0.7526	Intermediate Similarity	NPC242728
0.7515	Intermediate Similarity	NPC477217
0.7515	Intermediate Similarity	NPC313867
0.7515	Intermediate Similarity	NPC316008
0.7515	Intermediate Similarity	NPC201244
0.7515	Intermediate Similarity	NPC5620
0.7513	Intermediate Similarity	NPC477527
0.75	Intermediate Similarity	NPC469445
0.75	Intermediate Similarity	NPC149962
0.7475	Intermediate Similarity	NPC478008
0.7474	Intermediate Similarity	NPC194699
0.7474	Intermediate Similarity	NPC219350
0.747	Intermediate Similarity	NPC262077
0.7455	Intermediate Similarity	NPC315283
0.7455	Intermediate Similarity	NPC52748
0.7455	Intermediate Similarity	NPC314388
0.7442	Intermediate Similarity	NPC197743
0.7442	Intermediate Similarity	NPC326349
0.7442	Intermediate Similarity	NPC297145
0.7442	Intermediate Similarity	NPC323336
0.744	Intermediate Similarity	NPC245974
0.7438	Intermediate Similarity	NPC326966
0.7429	Intermediate Similarity	NPC22883
0.7429	Intermediate Similarity	NPC5719
0.7429	Intermediate Similarity	NPC217804
0.7429	Intermediate Similarity	NPC210377
0.7425	Intermediate Similarity	NPC225648
0.7425	Intermediate Similarity	NPC329761
0.7419	Intermediate Similarity	NPC29531
0.7413	Intermediate Similarity	NPC315804

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 NPC279871 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	125
0.1-0.2	410
0.2-0.3	742
0.3-0.4	1692
0.4-0.5	2773
0.5-0.6	2817
0.6-0.7	567
0.7-0.8	24
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
0.8072	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7131	Phase 3
0.7759	Intermediate Similarity	NPD7608	Discontinued
0.7706	Intermediate Similarity	NPD8019	Approved
0.7688	Intermediate Similarity	NPD8303	Discontinued
0.7566	Intermediate Similarity	NPD7810	Phase 3
0.7566	Intermediate Similarity	NPD7811	Phase 3
0.753	Intermediate Similarity	NPD8323	Discontinued
0.75	Intermediate Similarity	NPD7495	Discontinued
0.7401	Intermediate Similarity	NPD7485	Phase 3
0.7401	Intermediate Similarity	NPD7484	Phase 3
0.7394	Intermediate Similarity	NPD7978	Discontinued
0.7375	Intermediate Similarity	NPD3136	Phase 2
0.7333	Intermediate Similarity	NPD7450	Phase 2
0.7305	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6851	Approved
0.7297	Intermediate Similarity	NPD6853	Approved
0.7284	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD8172	Phase 2
0.7256	Intermediate Similarity	NPD8173	Phase 2
0.7232	Intermediate Similarity	NPD8031	Discontinued
0.722	Intermediate Similarity	NPD8356	Approved
0.7209	Intermediate Similarity	NPD7523	Phase 3
0.7189	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3125	Approved
0.7163	Intermediate Similarity	NPD8430	Approved
0.7151	Intermediate Similarity	NPD7303	Discontinued
0.7134	Intermediate Similarity	NPD6346	Approved
0.7128	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4659	Approved
0.709	Intermediate Similarity	NPD8025	Phase 2
0.7081	Intermediate Similarity	NPD6297	Approved
0.7059	Intermediate Similarity	NPD3400	Discontinued
0.7053	Intermediate Similarity	NPD7617	Discontinued
0.7052	Intermediate Similarity	NPD7613	Discontinued
0.7041	Intermediate Similarity	NPD6681	Discovery
0.7041	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD2888	Approved
0.7017	Intermediate Similarity	NPD2017	Approved
0.7017	Intermediate Similarity	NPD2890	Approved
0.7017	Intermediate Similarity	NPD2889	Approved
0.6989	Remote Similarity	NPD8417	Discontinued
0.6989	Remote Similarity	NPD5445	Approved
0.6977	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5745	Approved
0.6964	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5481	Discontinued
0.6944	Remote Similarity	NPD2098	Approved
0.694	Remote Similarity	NPD5137	Approved
0.6939	Remote Similarity	NPD7565	Approved
0.6937	Remote Similarity	NPD2584	Suspended
0.6935	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4103	Phase 2
0.6909	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1330	Phase 2
0.6901	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4652	Approved
0.6875	Remote Similarity	NPD8315	Phase 1
0.6868	Remote Similarity	NPD5823	Approved
0.6859	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6390	Discontinued
0.6848	Remote Similarity	NPD5746	Approved
0.6845	Remote Similarity	NPD6073	Approved
0.6839	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5967	Approved
0.6833	Remote Similarity	NPD2097	Approved
0.6821	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6294	Approved
0.6805	Remote Similarity	NPD6295	Approved
0.6788	Remote Similarity	NPD5203	Approved
0.6788	Remote Similarity	NPD5201	Approved
0.6788	Remote Similarity	NPD4617	Approved
0.6788	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4620	Approved
0.6786	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7972	Discontinued
0.6772	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5485	Approved
0.6755	Remote Similarity	NPD5484	Approved
0.675	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8162	Phase 2
0.675	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6088	Approved
0.6736	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6312	Discontinued
0.6733	Remote Similarity	NPD8161	Suspended
0.6727	Remote Similarity	NPD4177	Approved
0.6727	Remote Similarity	NPD4175	Approved
0.6726	Remote Similarity	NPD5119	Approved
0.6726	Remote Similarity	NPD5120	Approved
0.6726	Remote Similarity	NPD5121	Approved
0.6726	Remote Similarity	NPD8265	Approved
0.6726	Remote Similarity	NPD5296	Approved
0.6726	Remote Similarity	NPD8416	Discontinued
0.6721	Remote Similarity	NPD6862	Phase 2
0.6706	Remote Similarity	NPD3555	Approved
0.6706	Remote Similarity	NPD6852	Discontinued
0.6706	Remote Similarity	NPD3554	Approved
0.6706	Remote Similarity	NPD3552	Approved
0.6706	Remote Similarity	NPD3553	Approved
0.6702	Remote Similarity	NPD7281	Phase 3
0.6702	Remote Similarity	NPD7280	Phase 3
0.6702	Remote Similarity	NPD3965	Phase 1
0.67	Remote Similarity	NPD6255	Approved
0.67	Remote Similarity	NPD6256	Approved
0.67	Remote Similarity	NPD6254	Approved
0.6687	Remote Similarity	NPD4677	Discontinued
0.6686	Remote Similarity	NPD8643	Discontinued
0.6686	Remote Similarity	NPD8076	Discontinued
0.6685	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7714	Approved
0.6667	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5218	Approved
0.6667	Remote Similarity	NPD1753	Discontinued
0.6667	Remote Similarity	NPD5219	Approved
0.6667	Remote Similarity	NPD7451	Discontinued
0.6667	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6676	Phase 2
0.6667	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7715	Approved
0.665	Remote Similarity	NPD6253	Approved
0.6648	Remote Similarity	NPD7600	Phase 2
0.6647	Remote Similarity	NPD5725	Approved
0.663	Remote Similarity	NPD7011	Discontinued
0.663	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5355	Approved
0.663	Remote Similarity	NPD5356	Approved
0.6628	Remote Similarity	NPD1725	Approved
0.6627	Remote Similarity	NPD6623	Phase 3
0.6626	Remote Similarity	NPD2561	Approved
0.6626	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD2562	Approved
0.6625	Remote Similarity	NPD1759	Phase 1
0.6614	Remote Similarity	NPD5313	Approved
0.6614	Remote Similarity	NPD5312	Approved
0.6612	Remote Similarity	NPD8351	Phase 2
0.6611	Remote Similarity	NPD6502	Phase 2
0.661	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4619	Approved
0.6607	Remote Similarity	NPD4621	Approved
0.6606	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4576	Approved
0.6604	Remote Similarity	NPD4574	Approved
0.6596	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7599	Phase 2
0.6592	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6667	Approved
0.6591	Remote Similarity	NPD6666	Approved
0.6588	Remote Similarity	NPD555	Phase 2
0.6585	Remote Similarity	NPD7585	Approved
0.6582	Remote Similarity	NPD6505	Approved
0.6582	Remote Similarity	NPD6504	Approved
0.658	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5557	Phase 1
0.6579	Remote Similarity	NPD5190	Phase 2
0.6575	Remote Similarity	NPD7105	Phase 1
0.6575	Remote Similarity	NPD7110	Phase 1
0.6575	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD4731	Phase 3
0.6573	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1968	Approved
0.6571	Remote Similarity	NPD1967	Approved
0.6568	Remote Similarity	NPD5747	Discontinued
0.6564	Remote Similarity	NPD4435	Approved
0.6562	Remote Similarity	NPD1758	Phase 1
0.6557	Remote Similarity	NPD7737	Approved
0.6557	Remote Similarity	NPD7738	Approved
0.6556	Remote Similarity	NPD3455	Phase 2
0.6552	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2568	Approved
0.6548	Remote Similarity	NPD6039	Approved
0.6548	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.654	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3879	Approved
0.6537	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD7583	Approved
0.6536	Remote Similarity	NPD1670	Discontinued
0.6534	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD3692	Discontinued
0.6527	Remote Similarity	NPD4993	Discontinued
0.6526	Remote Similarity	NPD4603	Phase 2
0.6517	Remote Similarity	NPD3536	Discontinued
0.6513	Remote Similarity	NPD4434	Approved
0.6513	Remote Similarity	NPD7683	Discontinued
0.6512	Remote Similarity	NPD6901	Phase 3
0.6512	Remote Similarity	NPD5688	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