NPASS Compound

Structure

CID184848 OpenBabel06191715562D 38 41 0 0 1 0 0 0 0 0999 V2000 -2.8689 -3.6521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2134 -4.0035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4631 -1.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7746 1.9532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3885 2.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2660 2.4619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5410 -0.5253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8077 -2.0919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0814 -2.7455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8475 1.4669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6947 1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6938 -0.9780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2343 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3877 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8466 -1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6929 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9397 -3.3499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7368 -2.3941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9278 1.4649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8478 -2.4433 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6941 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 0.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6932 -0.9770 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5416 1.4664 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2345 1.4659 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8475 -1.4663 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5740 -3.0969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3882 1.9552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5413 0.4883 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9775 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9272 0.4873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5616 -1.4777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3712 -4.0527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5032 -2.7947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0814 1.9542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 4 21 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 8 32 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 17 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 31 1 0 0 0 0 17 32 1 0 0 0 0 18 25 1 0 0 0 0 18 33 1 0 0 0 0 19 20 1 0 0 0 0 21 34 2 0 0 0 0 21 38 1 0 0 0 0 22 11 1 6 0 0 0 22 28 1 0 0 0 0 22 29 1 0 0 0 0 23 24 2 0 0 0 0 23 31 1 0 0 0 0 24 33 1 0 0 0 0 25 28 1 0 0 0 0 25 35 1 1 0 0 0 26 30 1 0 0 0 0 26 31 1 6 0 0 0 27 30 1 0 0 0 0 27 38 1 6 0 0 0 28 32 1 6 0 0 0 29 36 2 0 0 0 0 29 37 1 0 0 0 0 31 7 1 6 0 0 0 32 33 1 6 0 0 0 33 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.38
Volume:	578.503
LogP:	5.697
LogD:	4.274
LogS:	-5.021
# Rotatable Bonds:	8
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.267
Synthetic Accessibility Score:	5.005
Fsp3:	0.818
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:	-5.235
MDCK Permeability:	1.5067839740368072e-05
Pgp-inhibitor:	0.752
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.048
30% Bioavailability (F30%):	0.239

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	92.74446868896484%
Volume Distribution (VD):	0.688
Pgp-substrate:	2.9087953567504883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.18
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.946
CYP2C9-inhibitor:	0.148
CYP2C9-substrate:	0.973
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.464
CYP3A4-inhibitor:	0.145
CYP3A4-substrate:	0.478

ADMET: Excretion

Clearance (CL):	2.441
Half-life (T1/2):	0.165

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.169
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.161
Maximum Recommended Daily Dose:	0.507
Skin Sensitization:	0.05
Carcinogencity:	0.03
Eye Corrosion:	0.006
Eye Irritation:	0.031
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC184848

Natural Product ID:	NPC184848
*Common Name:**	Pachymic Acid
IUPAC Name:	(2R)-2-[(3S,5R,10S,13R,14R,16R,17R)-3-acetyloxy-16-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms:	Pachymic Acid
Standard InCHIKey:	VDYCLYGKCGVBHN-DRCQUEPLSA-N
Standard InCHI:	InChI=1S/C33H52O5/c1-19(2)20(3)10-11-22(29(36)37)28-25(35)18-33(9)24-12-13-26-30(5,6)27(38-21(4)34)15-16-31(26,7)23(24)14-17-32(28,33)8/h19,22,25-28,35H,3,10-18H2,1-2,4-9H3,(H,36,37)/t22-,25-,26+,27+,28+,31-,32-,33+/m1/s1
SMILES:	CC(C)C(=C)CC[C@H]([C@H]1[C@@H](C[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1CC3)OC(=O)C)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468034
PubChem CID:	5484385
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
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO33546	Poria coco	Species		Eukaryota	n.a.	Yunnan, Kunming, China	n.a.	PMID[17488130]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO7611	Sclerotium poriae cocos	Species	Typhulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6117	Poria	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO7611	Sclerotium poriae cocos	Species	Typhulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	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	1
Others	6

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[460859]
NPT2586	Individual Protein	Phospholipase A2, acidic	Naja naja	IC50	=	2897000.0	nM	PMID[460860]
NPT2586	Individual Protein	Phospholipase A2, acidic	Naja naja	Inhibition	=	66.0	%	PMID[460860]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[460859]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	24.7	%	PMID[460859]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	71.6	%	PMID[460859]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	96.5	%	PMID[460859]

☑ 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 NPC184848 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	178
0.1-0.2	1204
0.2-0.3	5132
0.3-0.4	14199
0.4-0.5	7702
0.5-0.6	5593
0.6-0.7	6248
0.7-0.8	2134
0.8-0.85	223
0.85-0.9	51
0.9-0.95	25
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC69548
0.967	High Similarity	NPC477813
0.9659	High Similarity	NPC23434
0.9432	High Similarity	NPC474889
0.9341	High Similarity	NPC45324
0.9341	High Similarity	NPC162001
0.9341	High Similarity	NPC222845
0.9333	High Similarity	NPC470375
0.9333	High Similarity	NPC470376
0.9326	High Similarity	NPC148414
0.9326	High Similarity	NPC175628
0.9326	High Similarity	NPC111585
0.9318	High Similarity	NPC183546
0.9222	High Similarity	NPC26888
0.9213	High Similarity	NPC54689
0.9111	High Similarity	NPC471896
0.9101	High Similarity	NPC294480
0.9101	High Similarity	NPC242864
0.9091	High Similarity	NPC28252
0.9091	High Similarity	NPC212843
0.9091	High Similarity	NPC55309
0.9043	High Similarity	NPC48647
0.9043	High Similarity	NPC186810
0.9032	High Similarity	NPC120708
0.9011	High Similarity	NPC154101
0.9011	High Similarity	NPC297265
0.8989	High Similarity	NPC159046
0.8989	High Similarity	NPC233836
0.8989	High Similarity	NPC187376
0.8989	High Similarity	NPC312215
0.8925	High Similarity	NPC48330
0.8925	High Similarity	NPC469599
0.8913	High Similarity	NPC152897
0.8913	High Similarity	NPC66429
0.8913	High Similarity	NPC243866
0.8913	High Similarity	NPC470224
0.8901	High Similarity	NPC123854
0.8901	High Similarity	NPC469400
0.8901	High Similarity	NPC44240
0.883	High Similarity	NPC173272
0.8817	High Similarity	NPC159410
0.8804	High Similarity	NPC150383
0.8791	High Similarity	NPC77168
0.8791	High Similarity	NPC474704
0.8791	High Similarity	NPC475921
0.8791	High Similarity	NPC84271
0.8791	High Similarity	NPC102414
0.8791	High Similarity	NPC155479
0.8778	High Similarity	NPC474684
0.8778	High Similarity	NPC142361
0.8776	High Similarity	NPC472228
0.8776	High Similarity	NPC472227
0.8723	High Similarity	NPC470016
0.8723	High Similarity	NPC317586
0.8723	High Similarity	NPC279974
0.8723	High Similarity	NPC473648
0.8723	High Similarity	NPC263347
0.871	High Similarity	NPC141497
0.871	High Similarity	NPC107674
0.871	High Similarity	NPC170220
0.8696	High Similarity	NPC46281
0.8696	High Similarity	NPC20388
0.8687	High Similarity	NPC278628
0.8687	High Similarity	NPC231530
0.8687	High Similarity	NPC475494
0.8681	High Similarity	NPC247406
0.8681	High Similarity	NPC48866
0.8673	High Similarity	NPC140723
0.8667	High Similarity	NPC325594
0.866	High Similarity	NPC473514
0.8632	High Similarity	NPC95565
0.8632	High Similarity	NPC42042
0.8632	High Similarity	NPC155676
0.8617	High Similarity	NPC471720
0.8617	High Similarity	NPC7165
0.8617	High Similarity	NPC166906
0.8617	High Similarity	NPC469406
0.8602	High Similarity	NPC86266
0.8602	High Similarity	NPC189520
0.8602	High Similarity	NPC110657
0.8602	High Similarity	NPC160506
0.8602	High Similarity	NPC212301
0.8587	High Similarity	NPC474679
0.8586	High Similarity	NPC477812
0.8586	High Similarity	NPC96268
0.8571	High Similarity	NPC56498
0.8571	High Similarity	NPC473788
0.8571	High Similarity	NPC167877
0.8571	High Similarity	NPC475558
0.8571	High Similarity	NPC22388
0.8542	High Similarity	NPC57416
0.8542	High Similarity	NPC475894
0.8542	High Similarity	NPC107243
0.8529	High Similarity	NPC197428
0.8526	High Similarity	NPC20546
0.8526	High Similarity	NPC205173
0.8515	High Similarity	NPC94529
0.8511	High Similarity	NPC206810
0.8485	Intermediate Similarity	NPC236390
0.8485	Intermediate Similarity	NPC159442
0.8478	Intermediate Similarity	NPC4309
0.8469	Intermediate Similarity	NPC474327
0.8462	Intermediate Similarity	NPC155011
0.8462	Intermediate Similarity	NPC474970
0.8462	Intermediate Similarity	NPC6979
0.8462	Intermediate Similarity	NPC73038
0.8462	Intermediate Similarity	NPC94755
0.8462	Intermediate Similarity	NPC72133
0.8454	Intermediate Similarity	NPC477854
0.8454	Intermediate Similarity	NPC119036
0.8438	Intermediate Similarity	NPC253115
0.8438	Intermediate Similarity	NPC7124
0.8438	Intermediate Similarity	NPC96859
0.8438	Intermediate Similarity	NPC304899
0.8438	Intermediate Similarity	NPC305483
0.8438	Intermediate Similarity	NPC327179
0.8438	Intermediate Similarity	NPC327788
0.8438	Intermediate Similarity	NPC328162
0.8421	Intermediate Similarity	NPC111015
0.8421	Intermediate Similarity	NPC49670
0.8416	Intermediate Similarity	NPC220974
0.8404	Intermediate Similarity	NPC45269
0.84	Intermediate Similarity	NPC29705
0.84	Intermediate Similarity	NPC28656
0.8387	Intermediate Similarity	NPC474570
0.8387	Intermediate Similarity	NPC476733
0.8387	Intermediate Similarity	NPC215029
0.8384	Intermediate Similarity	NPC136289
0.8384	Intermediate Similarity	NPC473928
0.8384	Intermediate Similarity	NPC281702
0.8384	Intermediate Similarity	NPC204450
0.8384	Intermediate Similarity	NPC195290
0.837	Intermediate Similarity	NPC33768
0.8367	Intermediate Similarity	NPC307954
0.8367	Intermediate Similarity	NPC476274
0.8367	Intermediate Similarity	NPC316964
0.8367	Intermediate Similarity	NPC218383
0.8367	Intermediate Similarity	NPC205899
0.8365	Intermediate Similarity	NPC71348
0.8352	Intermediate Similarity	NPC474218
0.8351	Intermediate Similarity	NPC320306
0.8351	Intermediate Similarity	NPC18319
0.8351	Intermediate Similarity	NPC469432
0.8333	Intermediate Similarity	NPC195708
0.8333	Intermediate Similarity	NPC255809
0.8333	Intermediate Similarity	NPC471037
0.8317	Intermediate Similarity	NPC196528
0.8316	Intermediate Similarity	NPC474436
0.8316	Intermediate Similarity	NPC25750
0.8316	Intermediate Similarity	NPC470254
0.8316	Intermediate Similarity	NPC49776
0.8316	Intermediate Similarity	NPC63118
0.8316	Intermediate Similarity	NPC471902
0.8316	Intermediate Similarity	NPC86368
0.8316	Intermediate Similarity	NPC473690
0.8316	Intermediate Similarity	NPC287118
0.83	Intermediate Similarity	NPC55872
0.8298	Intermediate Similarity	NPC113989
0.8298	Intermediate Similarity	NPC227467
0.8298	Intermediate Similarity	NPC210037
0.8298	Intermediate Similarity	NPC477147
0.8298	Intermediate Similarity	NPC290614
0.8298	Intermediate Similarity	NPC273621
0.8298	Intermediate Similarity	NPC477872
0.8298	Intermediate Similarity	NPC7260
0.8298	Intermediate Similarity	NPC120840
0.8298	Intermediate Similarity	NPC18872
0.8298	Intermediate Similarity	NPC120968
0.8298	Intermediate Similarity	NPC477149
0.8286	Intermediate Similarity	NPC52634
0.8286	Intermediate Similarity	NPC202889
0.8283	Intermediate Similarity	NPC224720
0.8283	Intermediate Similarity	NPC476223
0.8283	Intermediate Similarity	NPC476240
0.8283	Intermediate Similarity	NPC99411
0.8283	Intermediate Similarity	NPC81530
0.828	Intermediate Similarity	NPC131470
0.828	Intermediate Similarity	NPC471722
0.828	Intermediate Similarity	NPC28227
0.828	Intermediate Similarity	NPC474719
0.828	Intermediate Similarity	NPC471724
0.828	Intermediate Similarity	NPC143767
0.8265	Intermediate Similarity	NPC10364
0.8265	Intermediate Similarity	NPC164349
0.8261	Intermediate Similarity	NPC2783
0.8261	Intermediate Similarity	NPC12774
0.8261	Intermediate Similarity	NPC264127
0.8252	Intermediate Similarity	NPC265655
0.8247	Intermediate Similarity	NPC328371
0.8247	Intermediate Similarity	NPC477853
0.8247	Intermediate Similarity	NPC125622
0.8242	Intermediate Similarity	NPC82902
0.8242	Intermediate Similarity	NPC165064
0.8242	Intermediate Similarity	NPC100391
0.8235	Intermediate Similarity	NPC42847
0.8235	Intermediate Similarity	NPC64844
0.8235	Intermediate Similarity	NPC44063
0.8229	Intermediate Similarity	NPC184870
0.8229	Intermediate Similarity	NPC303863
0.8229	Intermediate Similarity	NPC474922

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 NPC184848 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1598
0.2-0.3	3995
0.3-0.4	2318
0.4-0.5	585
0.5-0.6	179
0.6-0.7	162
0.7-0.8	146
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.871	High Similarity	NPD6399	Phase 3
0.8602	High Similarity	NPD8035	Phase 2
0.8602	High Similarity	NPD8034	Phase 2
0.85	High Similarity	NPD5739	Approved
0.85	High Similarity	NPD6675	Approved
0.85	High Similarity	NPD6402	Approved
0.85	High Similarity	NPD7128	Approved
0.8431	Intermediate Similarity	NPD6373	Approved
0.8431	Intermediate Similarity	NPD6372	Approved
0.8333	Intermediate Similarity	NPD6881	Approved
0.8333	Intermediate Similarity	NPD7320	Approved
0.8333	Intermediate Similarity	NPD6899	Approved
0.8269	Intermediate Similarity	NPD8130	Phase 1
0.8269	Intermediate Similarity	NPD6649	Approved
0.8269	Intermediate Similarity	NPD6650	Approved
0.8235	Intermediate Similarity	NPD5701	Approved
0.8235	Intermediate Similarity	NPD5697	Approved
0.819	Intermediate Similarity	NPD8297	Approved
0.8173	Intermediate Similarity	NPD7290	Approved
0.8173	Intermediate Similarity	NPD6883	Approved
0.8173	Intermediate Similarity	NPD7102	Approved
0.8163	Intermediate Similarity	NPD6084	Phase 2
0.8163	Intermediate Similarity	NPD6083	Phase 2
0.8163	Intermediate Similarity	NPD7902	Approved
0.8155	Intermediate Similarity	NPD6011	Approved
0.8152	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD5695	Phase 3
0.8125	Intermediate Similarity	NPD4202	Approved
0.8095	Intermediate Similarity	NPD6617	Approved
0.8095	Intermediate Similarity	NPD6847	Approved
0.8095	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD6869	Approved
0.8077	Intermediate Similarity	NPD6012	Approved
0.8077	Intermediate Similarity	NPD6013	Approved
0.8077	Intermediate Similarity	NPD6014	Approved
0.8065	Intermediate Similarity	NPD7334	Approved
0.8065	Intermediate Similarity	NPD6684	Approved
0.8065	Intermediate Similarity	NPD7146	Approved
0.8065	Intermediate Similarity	NPD3618	Phase 1
0.8065	Intermediate Similarity	NPD7521	Approved
0.8065	Intermediate Similarity	NPD6409	Approved
0.8065	Intermediate Similarity	NPD5330	Approved
0.8043	Intermediate Similarity	NPD4786	Approved
0.8041	Intermediate Similarity	NPD7748	Approved
0.8021	Intermediate Similarity	NPD5281	Approved
0.8021	Intermediate Similarity	NPD5284	Approved
0.8019	Intermediate Similarity	NPD6882	Approved
0.8	Intermediate Similarity	NPD5328	Approved
0.798	Intermediate Similarity	NPD4755	Approved
0.7959	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD5696	Approved
0.79	Intermediate Similarity	NPD7638	Approved
0.7895	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6903	Approved
0.7857	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7900	Approved
0.7849	Intermediate Similarity	NPD3665	Phase 1
0.7849	Intermediate Similarity	NPD3133	Approved
0.7849	Intermediate Similarity	NPD3666	Approved
0.7835	Intermediate Similarity	NPD6079	Approved
0.7835	Intermediate Similarity	NPD7515	Phase 2
0.7826	Intermediate Similarity	NPD3667	Approved
0.7822	Intermediate Similarity	NPD5286	Approved
0.7822	Intermediate Similarity	NPD5285	Approved
0.7822	Intermediate Similarity	NPD4700	Approved
0.7822	Intermediate Similarity	NPD4696	Approved
0.7822	Intermediate Similarity	NPD7640	Approved
0.7822	Intermediate Similarity	NPD7639	Approved
0.7788	Intermediate Similarity	NPD6008	Approved
0.7745	Intermediate Similarity	NPD5223	Approved
0.7708	Intermediate Similarity	NPD6672	Approved
0.7708	Intermediate Similarity	NPD5737	Approved
0.77	Intermediate Similarity	NPD4697	Phase 3
0.7684	Intermediate Similarity	NPD6098	Approved
0.767	Intermediate Similarity	NPD5225	Approved
0.767	Intermediate Similarity	NPD5211	Phase 2
0.767	Intermediate Similarity	NPD4633	Approved
0.767	Intermediate Similarity	NPD5224	Approved
0.767	Intermediate Similarity	NPD5226	Approved
0.7667	Intermediate Similarity	NPD6116	Phase 1
0.7658	Intermediate Similarity	NPD6335	Approved
0.7653	Intermediate Similarity	NPD6050	Approved
0.7636	Intermediate Similarity	NPD6274	Approved
0.7629	Intermediate Similarity	NPD6904	Approved
0.7629	Intermediate Similarity	NPD6673	Approved
0.7629	Intermediate Similarity	NPD6080	Approved
0.7629	Intermediate Similarity	NPD4753	Phase 2
0.7615	Intermediate Similarity	NPD4632	Approved
0.7609	Intermediate Similarity	NPD7525	Registered
0.7596	Intermediate Similarity	NPD5174	Approved
0.7596	Intermediate Similarity	NPD4754	Approved
0.7596	Intermediate Similarity	NPD5175	Approved
0.7589	Intermediate Similarity	NPD7101	Approved
0.7589	Intermediate Similarity	NPD7100	Approved
0.7568	Intermediate Similarity	NPD6317	Approved
0.7556	Intermediate Similarity	NPD6117	Approved
0.7551	Intermediate Similarity	NPD5207	Approved
0.7551	Intermediate Similarity	NPD5692	Phase 3
0.7525	Intermediate Similarity	NPD5221	Approved
0.7525	Intermediate Similarity	NPD5222	Approved
0.7525	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5141	Approved
0.75	Intermediate Similarity	NPD6313	Approved
0.75	Intermediate Similarity	NPD6001	Approved
0.75	Intermediate Similarity	NPD5279	Phase 3
0.75	Intermediate Similarity	NPD6314	Approved
0.7475	Intermediate Similarity	NPD5694	Approved
0.7475	Intermediate Similarity	NPD6411	Approved
0.7456	Intermediate Similarity	NPD6909	Approved
0.7456	Intermediate Similarity	NPD6908	Approved
0.7456	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4767	Approved
0.7453	Intermediate Similarity	NPD4768	Approved
0.7451	Intermediate Similarity	NPD5173	Approved
0.7447	Intermediate Similarity	NPD4221	Approved
0.7447	Intermediate Similarity	NPD4223	Phase 3
0.7426	Intermediate Similarity	NPD5210	Approved
0.7426	Intermediate Similarity	NPD4629	Approved
0.7411	Intermediate Similarity	NPD6009	Approved
0.7411	Intermediate Similarity	NPD7115	Discovery
0.7407	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5329	Approved
0.7391	Intermediate Similarity	NPD6118	Approved
0.7391	Intermediate Similarity	NPD6115	Approved
0.7391	Intermediate Similarity	NPD6114	Approved
0.7391	Intermediate Similarity	NPD6697	Approved
0.7383	Intermediate Similarity	NPD6412	Phase 2
0.7368	Intermediate Similarity	NPD6319	Approved
0.7368	Intermediate Similarity	NPD4788	Approved
0.7363	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5208	Approved
0.734	Intermediate Similarity	NPD4139	Approved
0.734	Intermediate Similarity	NPD4692	Approved
0.7333	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7632	Discontinued
0.7328	Intermediate Similarity	NPD7604	Phase 2
0.7321	Intermediate Similarity	NPD6868	Approved
0.732	Intermediate Similarity	NPD5690	Phase 2
0.732	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5280	Approved
0.732	Intermediate Similarity	NPD4694	Approved
0.7315	Intermediate Similarity	NPD5128	Approved
0.7315	Intermediate Similarity	NPD4730	Approved
0.7315	Intermediate Similarity	NPD4729	Approved
0.7304	Intermediate Similarity	NPD5983	Phase 2
0.73	Intermediate Similarity	NPD5693	Phase 1
0.7292	Intermediate Similarity	NPD4197	Approved
0.7292	Intermediate Similarity	NPD3668	Phase 3
0.7288	Intermediate Similarity	NPD8293	Discontinued
0.7273	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6051	Approved
0.7273	Intermediate Similarity	NPD6101	Approved
0.7265	Intermediate Similarity	NPD7492	Approved
0.7263	Intermediate Similarity	NPD6435	Approved
0.7253	Intermediate Similarity	NPD6942	Approved
0.7253	Intermediate Similarity	NPD7339	Approved
0.7234	Intermediate Similarity	NPD4748	Discontinued
0.7227	Intermediate Similarity	NPD7736	Approved
0.7217	Intermediate Similarity	NPD6054	Approved
0.7217	Intermediate Similarity	NPD6059	Approved
0.7203	Intermediate Similarity	NPD6336	Discontinued
0.7203	Intermediate Similarity	NPD6616	Approved
0.7188	Intermediate Similarity	NPD5362	Discontinued
0.7182	Intermediate Similarity	NPD5249	Phase 3
0.7182	Intermediate Similarity	NPD5251	Approved
0.7182	Intermediate Similarity	NPD5247	Approved
0.7182	Intermediate Similarity	NPD5250	Approved
0.7182	Intermediate Similarity	NPD5135	Approved
0.7182	Intermediate Similarity	NPD4634	Approved
0.7182	Intermediate Similarity	NPD5169	Approved
0.7182	Intermediate Similarity	NPD5248	Approved
0.7182	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5369	Approved
0.7143	Intermediate Similarity	NPD4690	Approved
0.7143	Intermediate Similarity	NPD7078	Approved
0.7143	Intermediate Similarity	NPD4693	Phase 3
0.7143	Intermediate Similarity	NPD5205	Approved
0.7143	Intermediate Similarity	NPD4138	Approved
0.7143	Intermediate Similarity	NPD4688	Approved
0.7143	Intermediate Similarity	NPD4689	Approved
0.7117	Intermediate Similarity	NPD5217	Approved
0.7117	Intermediate Similarity	NPD5216	Approved
0.7117	Intermediate Similarity	NPD5127	Approved
0.7117	Intermediate Similarity	NPD5215	Approved
0.7094	Intermediate Similarity	NPD6370	Approved
0.7087	Intermediate Similarity	NPD5654	Approved
0.7065	Intermediate Similarity	NPD3702	Approved
0.7059	Intermediate Similarity	NPD7507	Approved
0.7054	Intermediate Similarity	NPD6053	Discontinued
0.7053	Intermediate Similarity	NPD5368	Approved
0.7041	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6016	Approved
0.7009	Intermediate Similarity	NPD6015	Approved
0.6991	Remote Similarity	NPD8133	Approved
0.6952	Remote Similarity	NPD5959	Approved
0.6949	Remote Similarity	NPD5988	Approved
0.6947	Remote Similarity	NPD7645	Phase 2
0.6944	Remote Similarity	NPD6052	Approved
0.6937	Remote Similarity	NPD4061	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