NPASS Compound

Structure

NPC161674 OpenBabel07101719512D 75 83 0 0 1 0 0 0 0 0999 V2000 -4.2786 0.4940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0612 4.3140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0731 4.3140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0612 -2.3379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0731 -2.3379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7114 0.9881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8557 -1.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8557 -0.4940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8557 1.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8557 -1.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4229 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5671 0.4940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4229 2.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7114 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4229 1.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5671 0.4940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2786 -7.4107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9900 -1.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4229 -3.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1343 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8557 1.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2786 -4.4464 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1343 -6.9167 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9900 -0.4940 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7114 -0.9881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8557 0.4940 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4229 -0.9881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7114 1.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9900 0.4940 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9900 -7.4107 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8457 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8457 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8457 -6.9167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8457 0.9881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8457 -0.9881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8457 -5.9286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9900 1.4821 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1343 -3.9524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1343 -2.9643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7114 2.9643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9900 -1.4821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9900 -5.4345 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1343 0.9881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2786 -2.4702 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4229 0.9881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5671 3.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5671 -1.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7114 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8557 0.4940 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5671 1.4821 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2786 -8.3988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8457 -1.9762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2786 -5.4345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9900 1.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9900 -8.3988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7014 -0.4940 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7014 0.4940 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7014 -7.4107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7014 1.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7014 -1.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7014 -5.4345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9900 2.4702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8557 3.4583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4229 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4229 -2.9643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1343 -0.9881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1343 -5.9286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1343 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2786 -1.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9900 -4.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9900 -2.4702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2786 1.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 48 1 0 0 0 0 3 48 1 0 0 0 0 4 49 1 0 0 0 0 5 49 1 0 0 0 0 7 51 1 0 0 0 0 9 10 1 0 0 0 0 9 23 2 0 0 0 0 10 28 1 0 0 0 0 11 14 1 0 0 0 0 11 27 1 0 0 0 0 12 13 1 0 0 0 0 12 29 1 0 0 0 0 13 50 1 0 0 0 0 14 52 1 0 0 0 0 15 17 1 0 0 0 0 15 48 1 0 0 0 0 16 18 1 0 0 0 0 16 51 1 0 0 0 0 17 53 1 0 0 0 0 18 53 1 0 0 0 0 19 54 1 0 0 0 0 20 55 1 0 0 0 0 21 24 1 0 0 0 0 21 68 1 0 0 0 0 22 1 1 6 0 0 0 22 31 1 0 0 0 0 22 69 1 0 0 0 0 23 30 1 0 0 0 0 23 51 1 0 0 0 0 24 40 1 0 0 0 0 24 56 1 6 0 0 0 25 19 1 6 0 0 0 25 32 1 0 0 0 0 25 70 1 0 0 0 0 26 20 1 1 0 0 0 26 33 1 0 0 0 0 26 71 1 0 0 0 0 27 49 1 0 0 0 0 27 50 1 1 0 0 0 28 50 1 1 0 0 0 28 52 1 0 0 0 0 29 49 1 0 0 0 0 29 72 1 1 0 0 0 30 42 1 0 0 0 0 30 53 1 6 0 0 0 31 34 1 0 0 0 0 31 57 1 1 0 0 0 32 35 1 0 0 0 0 32 58 1 1 0 0 0 33 36 1 0 0 0 0 33 59 1 6 0 0 0 34 37 1 0 0 0 0 34 60 1 6 0 0 0 35 38 1 0 0 0 0 35 61 1 6 0 0 0 36 39 1 0 0 0 0 36 62 1 1 0 0 0 37 43 1 0 0 0 0 37 63 1 6 0 0 0 38 44 1 0 0 0 0 38 64 1 1 0 0 0 39 45 1 0 0 0 0 39 65 1 6 0 0 0 40 41 1 0 0 0 0 40 73 1 6 0 0 0 41 46 1 0 0 0 0 41 74 1 1 0 0 0 42 48 1 0 0 0 0 42 66 1 6 0 0 0 43 69 1 0 0 0 0 43 74 1 1 0 0 0 44 70 1 0 0 0 0 44 73 1 6 0 0 0 45 71 1 0 0 0 0 45 75 1 1 0 0 0 46 68 1 0 0 0 0 46 72 1 6 0 0 0 47 67 2 0 0 0 0 47 75 1 0 0 0 0 50 6 1 1 0 0 0 51 52 1 1 0 0 0 52 8 1 1 0 0 0 53 47 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1074.56
Volume:	1036.348
LogP:	2.245
LogD:	2.174
LogS:	-3.494
# Rotatable Bonds:	11
TPSA:	353.9
# H-Bond Aceptor:	22
# H-Bond Donor:	13
# Rings:	9
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.068
Synthetic Accessibility Score:	6.793
Fsp3:	0.943
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:	-5.977
MDCK Permeability:	0.00015094532864168286
Pgp-inhibitor:	0.971
Pgp-substrate:	0.307
Human Intestinal Absorption (HIA):	0.991
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	72.51671600341797%
Volume Distribution (VD):	0.064
Pgp-substrate:	14.497523307800293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.124
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.006

ADMET: Excretion

Clearance (CL):	0.174
Half-life (T1/2):	0.658

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.039
Carcinogencity:	0.009
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.33

Download Data

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

Natural Product: NPC161674

Natural Product ID:	NPC161674
*Common Name:**	Latifoloside C
IUPAC Name:	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-1-hydroxy-10-[(2S,3R,4S,5S)-5-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms:	Latifoloside C
Standard InCHIKey:	OWJMPCBRZTYZJR-MZRTYAAGSA-N
Standard InCHI:	InChI=1S/C53H86O22/c1-22-31(57)34(60)37(63)43(69-22)74-41-40(73-44-38(64)35(61)32(58)25(19-54)70-44)24(56)21-68-46(41)72-29-12-13-50(6)27(49(29,4)5)11-14-52(8)28(50)10-9-23-30-42(66)48(2,3)15-17-53(30,18-16-51(23,52)7)47(67)75-45-39(65)36(62)33(59)26(20-55)71-45/h9,22,24-46,54-66H,10-21H2,1-8H3/t22-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33+,34+,35-,36-,37+,38+,39+,40-,41+,42-,43-,44-,45-,46-,50-,51+,52+,53-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O)CO[C@H]([C@@H]2O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3[C@H](O)C(C)(C)CC2)C(=O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506924
PubChem CID:	44566326
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425145]
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479318]

☑ 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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1214	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	Inhibition	=	20.0	%	PMID[508233]

☑ 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 NPC161674 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	268
0.1-0.2	1722
0.2-0.3	4951
0.3-0.4	11258
0.4-0.5	10708
0.5-0.6	6469
0.6-0.7	4177
0.7-0.8	1883
0.8-0.85	566
0.85-0.9	281
0.9-0.95	191
0.95-1	223

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471384
0.9907	High Similarity	NPC68175
0.9907	High Similarity	NPC148417
0.9907	High Similarity	NPC136768
0.9907	High Similarity	NPC110633
0.9815	High Similarity	NPC36831
0.9813	High Similarity	NPC160415
0.9813	High Similarity	NPC58448
0.9811	High Similarity	NPC46665
0.9811	High Similarity	NPC473826
0.9811	High Similarity	NPC475287
0.9811	High Similarity	NPC124296
0.9811	High Similarity	NPC174720
0.9811	High Similarity	NPC241909
0.9811	High Similarity	NPC114304
0.9811	High Similarity	NPC133818
0.9811	High Similarity	NPC323341
0.9811	High Similarity	NPC309714
0.9811	High Similarity	NPC155410
0.9811	High Similarity	NPC295823
0.9811	High Similarity	NPC114287
0.9811	High Similarity	NPC251263
0.9811	High Similarity	NPC166422
0.9811	High Similarity	NPC258885
0.9811	High Similarity	NPC475467
0.9811	High Similarity	NPC219180
0.9811	High Similarity	NPC192600
0.9811	High Similarity	NPC151543
0.9722	High Similarity	NPC475119
0.9722	High Similarity	NPC473824
0.972	High Similarity	NPC60557
0.972	High Similarity	NPC305981
0.972	High Similarity	NPC298034
0.972	High Similarity	NPC475160
0.972	High Similarity	NPC79643
0.972	High Similarity	NPC119592
0.972	High Similarity	NPC236638
0.972	High Similarity	NPC76972
0.972	High Similarity	NPC123199
0.972	High Similarity	NPC43550
0.972	High Similarity	NPC261506
0.972	High Similarity	NPC71065
0.972	High Similarity	NPC293330
0.972	High Similarity	NPC202828
0.972	High Similarity	NPC4328
0.972	High Similarity	NPC161717
0.972	High Similarity	NPC475140
0.972	High Similarity	NPC41061
0.972	High Similarity	NPC67857
0.972	High Similarity	NPC70809
0.972	High Similarity	NPC469782
0.972	High Similarity	NPC204414
0.972	High Similarity	NPC250247
0.972	High Similarity	NPC294453
0.972	High Similarity	NPC471385
0.972	High Similarity	NPC57484
0.972	High Similarity	NPC227551
0.972	High Similarity	NPC54636
0.972	High Similarity	NPC65105
0.972	High Similarity	NPC309907
0.972	High Similarity	NPC224381
0.972	High Similarity	NPC100639
0.972	High Similarity	NPC476068
0.972	High Similarity	NPC473714
0.972	High Similarity	NPC471550
0.9717	High Similarity	NPC104400
0.9717	High Similarity	NPC139044
0.9717	High Similarity	NPC102439
0.9717	High Similarity	NPC128925
0.9717	High Similarity	NPC256798
0.9717	High Similarity	NPC104071
0.9717	High Similarity	NPC10320
0.9717	High Similarity	NPC324875
0.9717	High Similarity	NPC276093
0.9717	High Similarity	NPC257468
0.9717	High Similarity	NPC475504
0.9717	High Similarity	NPC469946
0.9717	High Similarity	NPC475516
0.9717	High Similarity	NPC471383
0.9717	High Similarity	NPC101744
0.9717	High Similarity	NPC473373
0.9717	High Similarity	NPC109079
0.9717	High Similarity	NPC79718
0.9717	High Similarity	NPC292677
0.9636	High Similarity	NPC268184
0.963	High Similarity	NPC37134
0.963	High Similarity	NPC288205
0.963	High Similarity	NPC75287
0.963	High Similarity	NPC291903
0.963	High Similarity	NPC476992
0.963	High Similarity	NPC51465
0.963	High Similarity	NPC305267
0.963	High Similarity	NPC26626
0.9626	High Similarity	NPC73318
0.9626	High Similarity	NPC47063
0.9626	High Similarity	NPC150400
0.9626	High Similarity	NPC134835
0.9626	High Similarity	NPC163183
0.9626	High Similarity	NPC204458
0.9626	High Similarity	NPC96641
0.9626	High Similarity	NPC473343
0.9626	High Similarity	NPC138334
0.9626	High Similarity	NPC189884
0.9623	High Similarity	NPC473481
0.9623	High Similarity	NPC297208
0.9623	High Similarity	NPC235841
0.9623	High Similarity	NPC30397
0.9623	High Similarity	NPC164419
0.9623	High Similarity	NPC108748
0.9623	High Similarity	NPC191763
0.9623	High Similarity	NPC211798
0.9545	High Similarity	NPC207738
0.9541	High Similarity	NPC220160
0.9541	High Similarity	NPC102505
0.9541	High Similarity	NPC475514
0.9541	High Similarity	NPC69811
0.9541	High Similarity	NPC33012
0.9541	High Similarity	NPC104137
0.9541	High Similarity	NPC185466
0.9541	High Similarity	NPC470876
0.9541	High Similarity	NPC123522
0.9541	High Similarity	NPC85154
0.9541	High Similarity	NPC286457
0.9541	High Similarity	NPC473452
0.9541	High Similarity	NPC8524
0.9541	High Similarity	NPC309223
0.9541	High Similarity	NPC475209
0.9541	High Similarity	NPC191827
0.9541	High Similarity	NPC300419
0.9537	High Similarity	NPC164389
0.9537	High Similarity	NPC475486
0.9533	High Similarity	NPC116794
0.9533	High Similarity	NPC139894
0.9533	High Similarity	NPC473383
0.9533	High Similarity	NPC46388
0.9533	High Similarity	NPC37739
0.9528	High Similarity	NPC127056
0.9528	High Similarity	NPC174679
0.9528	High Similarity	NPC90856
0.9528	High Similarity	NPC270667
0.9528	High Similarity	NPC29069
0.9528	High Similarity	NPC475296
0.9528	High Similarity	NPC164194
0.9528	High Similarity	NPC274507
0.9528	High Similarity	NPC56713
0.9528	High Similarity	NPC136877
0.9528	High Similarity	NPC474589
0.9528	High Similarity	NPC279554
0.9528	High Similarity	NPC59804
0.9455	High Similarity	NPC109588
0.9455	High Similarity	NPC237191
0.9455	High Similarity	NPC473459
0.9455	High Similarity	NPC105800
0.9455	High Similarity	NPC232237
0.9455	High Similarity	NPC475899
0.9444	High Similarity	NPC269315
0.9444	High Similarity	NPC271138
0.9439	High Similarity	NPC179434
0.9434	High Similarity	NPC306746
0.9434	High Similarity	NPC57362
0.9434	High Similarity	NPC167383
0.9434	High Similarity	NPC237503
0.9434	High Similarity	NPC204407
0.9369	High Similarity	NPC192791
0.9369	High Similarity	NPC25663
0.9369	High Similarity	NPC477464
0.9369	High Similarity	NPC471577
0.9369	High Similarity	NPC51564
0.9369	High Similarity	NPC135849
0.9369	High Similarity	NPC473386
0.9364	High Similarity	NPC471547
0.9364	High Similarity	NPC323359
0.9364	High Similarity	NPC471580
0.9358	High Similarity	NPC475633
0.9352	High Similarity	NPC80843
0.9352	High Similarity	NPC1046
0.9346	High Similarity	NPC68419
0.9346	High Similarity	NPC475501
0.9346	High Similarity	NPC476885
0.9346	High Similarity	NPC102914
0.9346	High Similarity	NPC476881
0.9346	High Similarity	NPC108709
0.9346	High Similarity	NPC476882
0.9346	High Similarity	NPC7870
0.9346	High Similarity	NPC476883
0.9346	High Similarity	NPC110139
0.9346	High Similarity	NPC78046
0.9346	High Similarity	NPC476887
0.9346	High Similarity	NPC476880
0.9346	High Similarity	NPC476886
0.9346	High Similarity	NPC269095
0.9346	High Similarity	NPC476884
0.9346	High Similarity	NPC75747
0.9346	High Similarity	NPC199457
0.934	High Similarity	NPC476123
0.934	High Similarity	NPC28198
0.934	High Similarity	NPC284807
0.934	High Similarity	NPC177246
0.9292	High Similarity	NPC475591
0.9292	High Similarity	NPC4749

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 NPC161674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	2022
0.2-0.3	3828
0.3-0.4	1979
0.4-0.5	627
0.5-0.6	292
0.6-0.7	122
0.7-0.8	29
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8879	High Similarity	NPD8328	Phase 3
0.885	High Similarity	NPD8295	Clinical (unspecified phase)
0.8727	High Similarity	NPD8132	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD8133	Approved
0.7934	Intermediate Similarity	NPD8515	Approved
0.7934	Intermediate Similarity	NPD8516	Approved
0.7934	Intermediate Similarity	NPD8517	Approved
0.7895	Intermediate Similarity	NPD6412	Phase 2
0.7851	Intermediate Similarity	NPD8377	Approved
0.7851	Intermediate Similarity	NPD8294	Approved
0.7826	Intermediate Similarity	NPD6686	Approved
0.7818	Intermediate Similarity	NPD7902	Approved
0.7787	Intermediate Similarity	NPD8380	Approved
0.7787	Intermediate Similarity	NPD8379	Approved
0.7787	Intermediate Similarity	NPD8335	Approved
0.7787	Intermediate Similarity	NPD8513	Phase 3
0.7787	Intermediate Similarity	NPD8378	Approved
0.7787	Intermediate Similarity	NPD8296	Approved
0.7787	Intermediate Similarity	NPD8033	Approved
0.7706	Intermediate Similarity	NPD7748	Approved
0.768	Intermediate Similarity	NPD7507	Approved
0.7545	Intermediate Similarity	NPD7900	Approved
0.7545	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD7319	Approved
0.7479	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD7736	Approved
0.7398	Intermediate Similarity	NPD7327	Approved
0.7398	Intermediate Similarity	NPD7328	Approved
0.7339	Intermediate Similarity	NPD7516	Approved
0.7265	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7503	Approved
0.7209	Intermediate Similarity	NPD8293	Discontinued
0.7207	Intermediate Similarity	NPD8035	Phase 2
0.7207	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7031	Intermediate Similarity	NPD6370	Approved
0.6992	Remote Similarity	NPD6882	Approved
0.6992	Remote Similarity	NPD8297	Approved
0.6983	Remote Similarity	NPD7638	Approved
0.6942	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7640	Approved
0.6923	Remote Similarity	NPD7492	Approved
0.6923	Remote Similarity	NPD7639	Approved
0.6905	Remote Similarity	NPD6009	Approved
0.6905	Remote Similarity	NPD7115	Discovery
0.6887	Remote Similarity	NPD7645	Phase 2
0.6885	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6373	Approved
0.6885	Remote Similarity	NPD6372	Approved
0.6875	Remote Similarity	NPD6059	Approved
0.6875	Remote Similarity	NPD6319	Approved
0.6875	Remote Similarity	NPD6054	Approved
0.687	Remote Similarity	NPD6616	Approved
0.6846	Remote Similarity	NPD6067	Discontinued
0.6842	Remote Similarity	NPD8171	Discontinued
0.6829	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8074	Phase 3
0.6818	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7078	Approved
0.68	Remote Similarity	NPD4632	Approved
0.6777	Remote Similarity	NPD7128	Approved
0.6777	Remote Similarity	NPD5739	Approved
0.6777	Remote Similarity	NPD6675	Approved
0.6777	Remote Similarity	NPD6402	Approved
0.6774	Remote Similarity	NPD6650	Approved
0.6774	Remote Similarity	NPD6649	Approved
0.6765	Remote Similarity	NPD8450	Suspended
0.6754	Remote Similarity	NPD6411	Approved
0.6695	Remote Similarity	NPD4225	Approved
0.6692	Remote Similarity	NPD6015	Approved
0.6692	Remote Similarity	NPD6016	Approved
0.6691	Remote Similarity	NPD8449	Approved
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6641	Remote Similarity	NPD5988	Approved
0.664	Remote Similarity	NPD8130	Phase 1
0.6639	Remote Similarity	NPD6008	Approved
0.6607	Remote Similarity	NPD3618	Phase 1
0.6585	Remote Similarity	NPD5701	Approved
0.6585	Remote Similarity	NPD5697	Approved
0.6585	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6101	Approved
0.6577	Remote Similarity	NPD4786	Approved
0.656	Remote Similarity	NPD7102	Approved
0.656	Remote Similarity	NPD6883	Approved
0.656	Remote Similarity	NPD7290	Approved
0.6555	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD3667	Approved
0.6508	Remote Similarity	NPD6847	Approved
0.6508	Remote Similarity	NPD6617	Approved
0.6508	Remote Similarity	NPD6869	Approved
0.6491	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3669	Approved
0.6486	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6013	Approved
0.648	Remote Similarity	NPD6014	Approved
0.648	Remote Similarity	NPD6012	Approved
0.6471	Remote Similarity	NPD6083	Phase 2
0.6471	Remote Similarity	NPD6084	Phase 2
0.6466	Remote Similarity	NPD7604	Phase 2
0.6466	Remote Similarity	NPD7983	Approved
0.6439	Remote Similarity	NPD6921	Approved
0.6439	Remote Similarity	NPD5983	Phase 2
0.6435	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5328	Approved
0.641	Remote Similarity	NPD5778	Approved
0.641	Remote Similarity	NPD5779	Approved
0.6404	Remote Similarity	NPD3573	Approved
0.64	Remote Similarity	NPD6011	Approved
0.6397	Remote Similarity	NPD6033	Approved
0.6393	Remote Similarity	NPD7632	Discontinued
0.6378	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.637	Remote Similarity	NPD6336	Discontinued
0.6333	Remote Similarity	NPD4755	Approved
0.6325	Remote Similarity	NPD6079	Approved
0.6324	Remote Similarity	NPD8448	Approved
0.6316	Remote Similarity	NPD7146	Approved
0.6316	Remote Similarity	NPD7334	Approved
0.6316	Remote Similarity	NPD7521	Approved
0.6316	Remote Similarity	NPD5330	Approved
0.6316	Remote Similarity	NPD6409	Approved
0.6316	Remote Similarity	NPD6684	Approved
0.6308	Remote Similarity	NPD6940	Discontinued
0.6306	Remote Similarity	NPD1780	Approved
0.6306	Remote Similarity	NPD1779	Approved
0.6304	Remote Similarity	NPD8390	Approved
0.6304	Remote Similarity	NPD8391	Approved
0.6304	Remote Similarity	NPD8392	Approved
0.6299	Remote Similarity	NPD4634	Approved
0.6296	Remote Similarity	NPD8340	Approved
0.6296	Remote Similarity	NPD8299	Approved
0.6296	Remote Similarity	NPD8342	Approved
0.6296	Remote Similarity	NPD8341	Approved
0.6281	Remote Similarity	NPD5696	Approved
0.6271	Remote Similarity	NPD4202	Approved
0.626	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4697	Phase 3
0.625	Remote Similarity	NPD8451	Approved
0.623	Remote Similarity	NPD5286	Approved
0.623	Remote Similarity	NPD5285	Approved
0.623	Remote Similarity	NPD4696	Approved
0.623	Remote Similarity	NPD4700	Approved
0.6216	Remote Similarity	NPD7525	Registered
0.6216	Remote Similarity	NPD7625	Phase 1
0.6212	Remote Similarity	NPD7641	Discontinued
0.6207	Remote Similarity	NPD6672	Approved
0.6207	Remote Similarity	NPD6903	Approved
0.6207	Remote Similarity	NPD5737	Approved
0.6183	Remote Similarity	NPD6274	Approved
0.6182	Remote Similarity	NPD6114	Approved
0.6182	Remote Similarity	NPD6118	Approved
0.6182	Remote Similarity	NPD6697	Approved
0.6182	Remote Similarity	NPD6115	Approved
0.6179	Remote Similarity	NPD5344	Discontinued
0.6167	Remote Similarity	NPD5695	Phase 3
0.6167	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD7101	Approved
0.6165	Remote Similarity	NPD7100	Approved
0.6159	Remote Similarity	NPD8336	Approved
0.6159	Remote Similarity	NPD8337	Approved
0.614	Remote Similarity	NPD3666	Approved
0.614	Remote Similarity	NPD3665	Phase 1
0.614	Remote Similarity	NPD3668	Phase 3
0.614	Remote Similarity	NPD3133	Approved
0.6129	Remote Similarity	NPD5224	Approved
0.6129	Remote Similarity	NPD5211	Phase 2
0.6129	Remote Similarity	NPD4633	Approved
0.6129	Remote Similarity	NPD5226	Approved
0.6129	Remote Similarity	NPD5225	Approved
0.6116	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD7839	Suspended
0.6116	Remote Similarity	NPD5222	Approved
0.6116	Remote Similarity	NPD5221	Approved
0.6111	Remote Similarity	NPD4767	Approved
0.6111	Remote Similarity	NPD4768	Approved
0.6103	Remote Similarity	NPD7830	Approved
0.6103	Remote Similarity	NPD7829	Approved
0.6102	Remote Similarity	NPD7838	Discovery
0.6091	Remote Similarity	NPD6116	Phase 1
0.609	Remote Similarity	NPD6335	Approved
0.608	Remote Similarity	NPD5175	Approved
0.608	Remote Similarity	NPD5174	Approved
0.6077	Remote Similarity	NPD6053	Discontinued
0.6074	Remote Similarity	NPD6908	Approved
0.6074	Remote Similarity	NPD8444	Approved
0.6074	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD6909	Approved
0.6066	Remote Similarity	NPD5173	Approved
0.6063	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6868	Approved
0.6051	Remote Similarity	NPD8455	Phase 2
0.605	Remote Similarity	NPD7637	Suspended
0.6048	Remote Similarity	NPD5223	Approved
0.6047	Remote Similarity	NPD6371	Approved
0.6032	Remote Similarity	NPD5141	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