NPASS Compound

Structure

CID45269 OpenBabel06191715382D 37 39 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 5.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4905 3.8204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5394 3.5114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2308 4.6974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5981 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7473 4.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 -2.5388 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 2.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5981 1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 3.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 1.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4164 5.2327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 18 1 0 0 0 0 3 19 2 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 23 2 0 0 0 0 13 16 1 0 0 0 0 13 22 2 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 24 1 0 0 0 0 17 31 1 0 0 0 0 18 21 1 0 0 0 0 19 28 1 0 0 0 0 20 26 1 0 0 0 0 20 27 1 0 0 0 0 21 29 1 6 0 0 0 22 23 1 0 0 0 0 22 29 1 0 0 0 0 23 31 1 0 0 0 0 24 26 1 0 0 0 0 24 32 1 1 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 26 30 1 6 0 0 0 27 35 2 0 0 0 0 27 36 1 0 0 0 0 28 37 1 0 0 0 0 29 6 1 6 0 0 0 30 31 1 6 0 0 0 31 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.33
Volume:	555.985
LogP:	4.156
LogD:	1.731
LogS:	-3.783
# Rotatable Bonds:	10
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.269
Synthetic Accessibility Score:	5.362
Fsp3:	0.677
Lipinski Rule-of-5:	Accepted
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:	-5.719
MDCK Permeability:	2.0426950868568383e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.404
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.104
Plasma Protein Binding (PPB):	81.41825103759766%
Volume Distribution (VD):	0.449
Pgp-substrate:	10.582282066345215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.129
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.529
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.046

ADMET: Excretion

Clearance (CL):	1.564
Half-life (T1/2):	0.776

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.649
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.219
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.665
Carcinogencity:	0.663
Eye Corrosion:	0.005
Eye Irritation:	0.012
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC45269

Natural Product ID:	NPC45269
*Common Name:**	Poricoic Acid D
IUPAC Name:	2-[(2R,3R,3aR,6S,7S,9bR)-6-(2-carboxyethyl)-2-hydroxy-3a,6,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,4,7,8-hexahydrocyclopenta[a]naphthalen-3-yl]-6-hydroxy-6-methyl-5-methylideneheptanoic acid
Synonyms:	Poricoic Acid D
Standard InCHIKey:	DJHQMAXOQISYNY-OHUXFVNZSA-N
Standard InCHI:	InChI=1S/C31H46O6/c1-18(2)21-11-12-23-22(29(21,6)15-14-25(33)34)13-16-30(7)26(24(32)17-31(23,30)8)20(27(35)36)10-9-19(3)28(4,5)37/h12-13,20-21,24,26,32,37H,1,3,9-11,14-17H2,2,4-8H3,(H,33,34)(H,35,36)/t20?,21-,24+,26-,29-,30+,31-/m0/s1
SMILES:	C=C(C)[C@@H]1CC=C2C(=CC[C@]3(C)[C@@H](C(CCC(=C)C(C)(C)O)C(=O)O)[C@@H](C[C@@]23C)O)[C@@]1(C)CCC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227056
PubChem CID:	44424827
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]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	sclerotium	n.a.	PMID[21250700]
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]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	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]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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
Others	5

Activity Type	# Activity
Cell Line	1
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[448551]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[448551]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	15.3	%	PMID[448551]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	56.1	%	PMID[448551]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	81.5	%	PMID[448551]

☑ 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 NPC45269 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	174
0.1-0.2	966
0.2-0.3	4860
0.3-0.4	14503
0.4-0.5	9028
0.5-0.6	7285
0.6-0.7	4881
0.7-0.8	911
0.8-0.85	58
0.85-0.9	15
0.9-0.95	10
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.977	High Similarity	NPC7165
0.9647	High Similarity	NPC48866
0.9647	High Similarity	NPC247406
0.9551	High Similarity	NPC155676
0.9535	High Similarity	NPC155479
0.9444	High Similarity	NPC469432
0.9438	High Similarity	NPC20546
0.9425	High Similarity	NPC46281
0.9425	High Similarity	NPC123854
0.9341	High Similarity	NPC186810
0.9302	High Similarity	NPC312215
0.9213	High Similarity	NPC152897
0.9213	High Similarity	NPC66429
0.9213	High Similarity	NPC243866
0.9195	High Similarity	NPC294480
0.9186	High Similarity	NPC212843
0.913	High Similarity	NPC48647
0.9059	High Similarity	NPC310470
0.9011	High Similarity	NPC162001
0.9011	High Similarity	NPC263347
0.9011	High Similarity	NPC222845
0.9011	High Similarity	NPC45324
0.8977	High Similarity	NPC183546
0.8876	High Similarity	NPC54689
0.8817	High Similarity	NPC107243
0.8736	High Similarity	NPC165064
0.8723	High Similarity	NPC166745
0.8723	High Similarity	NPC235464
0.8723	High Similarity	NPC477813
0.8696	High Similarity	NPC469406
0.8681	High Similarity	NPC23434
0.8681	High Similarity	NPC154101
0.8617	High Similarity	NPC57416
0.8588	High Similarity	NPC196827
0.8588	High Similarity	NPC274996
0.8587	High Similarity	NPC472942
0.8587	High Similarity	NPC470376
0.8587	High Similarity	NPC470375
0.8571	High Similarity	NPC469400
0.8571	High Similarity	NPC69622
0.8506	High Similarity	NPC296367
0.8462	Intermediate Similarity	NPC214387
0.8462	Intermediate Similarity	NPC102414
0.8462	Intermediate Similarity	NPC84271
0.8462	Intermediate Similarity	NPC77168
0.8454	Intermediate Similarity	NPC204450
0.8454	Intermediate Similarity	NPC195290
0.8438	Intermediate Similarity	NPC218383
0.8421	Intermediate Similarity	NPC475894
0.8404	Intermediate Similarity	NPC184848
0.8404	Intermediate Similarity	NPC69548
0.837	Intermediate Similarity	NPC477147
0.837	Intermediate Similarity	NPC477149
0.8367	Intermediate Similarity	NPC236390
0.8351	Intermediate Similarity	NPC146822
0.8351	Intermediate Similarity	NPC99411
0.8333	Intermediate Similarity	NPC469994
0.8333	Intermediate Similarity	NPC197386
0.8283	Intermediate Similarity	NPC477812
0.828	Intermediate Similarity	NPC150383
0.828	Intermediate Similarity	NPC204341
0.8261	Intermediate Similarity	NPC2983
0.8261	Intermediate Similarity	NPC476733
0.8261	Intermediate Similarity	NPC215029
0.8242	Intermediate Similarity	NPC167877
0.8242	Intermediate Similarity	NPC317590
0.8242	Intermediate Similarity	NPC159046
0.8242	Intermediate Similarity	NPC233836
0.8242	Intermediate Similarity	NPC187376
0.8222	Intermediate Similarity	NPC474083
0.8222	Intermediate Similarity	NPC474218
0.8211	Intermediate Similarity	NPC469599
0.8202	Intermediate Similarity	NPC69279
0.8202	Intermediate Similarity	NPC83569
0.8191	Intermediate Similarity	NPC206810
0.8172	Intermediate Similarity	NPC320026
0.8172	Intermediate Similarity	NPC171441
0.8163	Intermediate Similarity	NPC474327
0.8152	Intermediate Similarity	NPC44181
0.8152	Intermediate Similarity	NPC242864
0.8144	Intermediate Similarity	NPC471717
0.8144	Intermediate Similarity	NPC10364
0.8132	Intermediate Similarity	NPC28252
0.8132	Intermediate Similarity	NPC89077
0.8132	Intermediate Similarity	NPC155011
0.8132	Intermediate Similarity	NPC55309
0.8125	Intermediate Similarity	NPC472941
0.8125	Intermediate Similarity	NPC456
0.8125	Intermediate Similarity	NPC173272
0.8125	Intermediate Similarity	NPC235053
0.8111	Intermediate Similarity	NPC194937
0.8111	Intermediate Similarity	NPC82902
0.8111	Intermediate Similarity	NPC476038
0.8105	Intermediate Similarity	NPC49670
0.809	Intermediate Similarity	NPC133391
0.8085	Intermediate Similarity	NPC107690
0.8085	Intermediate Similarity	NPC297265
0.8065	Intermediate Similarity	NPC477943
0.8065	Intermediate Similarity	NPC310236
0.8065	Intermediate Similarity	NPC474704
0.8065	Intermediate Similarity	NPC475921
0.8061	Intermediate Similarity	NPC241221
0.8061	Intermediate Similarity	NPC154072
0.8061	Intermediate Similarity	NPC205899
0.8061	Intermediate Similarity	NPC287833
0.8061	Intermediate Similarity	NPC51370
0.8061	Intermediate Similarity	NPC476274
0.8043	Intermediate Similarity	NPC142361
0.8043	Intermediate Similarity	NPC136548
0.8043	Intermediate Similarity	NPC96496
0.8043	Intermediate Similarity	NPC474684
0.8043	Intermediate Similarity	NPC136948
0.8043	Intermediate Similarity	NPC128644
0.8041	Intermediate Similarity	NPC18319
0.8022	Intermediate Similarity	NPC269638
0.8022	Intermediate Similarity	NPC283733
0.8022	Intermediate Similarity	NPC471224
0.8021	Intermediate Similarity	NPC472932
0.8021	Intermediate Similarity	NPC48330
0.8021	Intermediate Similarity	NPC173875
0.8021	Intermediate Similarity	NPC318282
0.8021	Intermediate Similarity	NPC174948
0.8021	Intermediate Similarity	NPC469995
0.8	Intermediate Similarity	NPC214697
0.8	Intermediate Similarity	NPC250575
0.8	Intermediate Similarity	NPC477373
0.8	Intermediate Similarity	NPC470254
0.8	Intermediate Similarity	NPC25750
0.798	Intermediate Similarity	NPC476223
0.798	Intermediate Similarity	NPC476240
0.798	Intermediate Similarity	NPC302537
0.798	Intermediate Similarity	NPC163372
0.798	Intermediate Similarity	NPC224720
0.7979	Intermediate Similarity	NPC111585
0.7979	Intermediate Similarity	NPC148414
0.7979	Intermediate Similarity	NPC175628
0.7978	Intermediate Similarity	NPC201912
0.7978	Intermediate Similarity	NPC38350
0.7957	Intermediate Similarity	NPC193843
0.7957	Intermediate Similarity	NPC470417
0.7957	Intermediate Similarity	NPC249889
0.7955	Intermediate Similarity	NPC477371
0.7941	Intermediate Similarity	NPC42847
0.7941	Intermediate Similarity	NPC64844
0.7938	Intermediate Similarity	NPC250757
0.7938	Intermediate Similarity	NPC301534
0.7938	Intermediate Similarity	NPC322063
0.7938	Intermediate Similarity	NPC328371
0.7935	Intermediate Similarity	NPC475007
0.7935	Intermediate Similarity	NPC473226
0.7935	Intermediate Similarity	NPC473168
0.7921	Intermediate Similarity	NPC472228
0.7921	Intermediate Similarity	NPC472227
0.7917	Intermediate Similarity	NPC292793
0.7912	Intermediate Similarity	NPC263974
0.7912	Intermediate Similarity	NPC473246
0.7912	Intermediate Similarity	NPC100391
0.7912	Intermediate Similarity	NPC164577
0.79	Intermediate Similarity	NPC234892
0.79	Intermediate Similarity	NPC473928
0.79	Intermediate Similarity	NPC293753
0.79	Intermediate Similarity	NPC308726
0.79	Intermediate Similarity	NPC56498
0.79	Intermediate Similarity	NPC119601
0.7895	Intermediate Similarity	NPC19114
0.7895	Intermediate Similarity	NPC26888
0.7895	Intermediate Similarity	NPC212301
0.7895	Intermediate Similarity	NPC212948
0.7895	Intermediate Similarity	NPC86266
0.7895	Intermediate Similarity	NPC110657
0.7895	Intermediate Similarity	NPC189520
0.7889	Intermediate Similarity	NPC260956
0.7889	Intermediate Similarity	NPC170985
0.7872	Intermediate Similarity	NPC474889
0.7872	Intermediate Similarity	NPC472971
0.7872	Intermediate Similarity	NPC472970
0.7872	Intermediate Similarity	NPC76879
0.7872	Intermediate Similarity	NPC262043
0.7872	Intermediate Similarity	NPC123912
0.7857	Intermediate Similarity	NPC320306
0.7849	Intermediate Similarity	NPC287079
0.7849	Intermediate Similarity	NPC90652
0.7841	Intermediate Similarity	NPC179028
0.7841	Intermediate Similarity	NPC321514
0.7835	Intermediate Similarity	NPC37646
0.7835	Intermediate Similarity	NPC53565
0.7835	Intermediate Similarity	NPC127063
0.7835	Intermediate Similarity	NPC241156
0.7835	Intermediate Similarity	NPC171395
0.7835	Intermediate Similarity	NPC476174
0.7822	Intermediate Similarity	NPC183570
0.7822	Intermediate Similarity	NPC111323
0.7822	Intermediate Similarity	NPC140723
0.7822	Intermediate Similarity	NPC55872
0.7812	Intermediate Similarity	NPC141497
0.7812	Intermediate Similarity	NPC170220
0.7812	Intermediate Similarity	NPC107674
0.7812	Intermediate Similarity	NPC472930
0.7812	Intermediate Similarity	NPC470224
0.7802	Intermediate Similarity	NPC97913

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 NPC45269 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1472
0.2-0.3	3886
0.3-0.4	2469
0.4-0.5	656
0.5-0.6	236
0.6-0.7	212
0.7-0.8	63
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8478	Intermediate Similarity	NPD5284	Approved
0.8478	Intermediate Similarity	NPD5281	Approved
0.8	Intermediate Similarity	NPD6399	Phase 3
0.7857	Intermediate Similarity	NPD6083	Phase 2
0.7857	Intermediate Similarity	NPD6084	Phase 2
0.7841	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD5695	Phase 3
0.7802	Intermediate Similarity	NPD5362	Discontinued
0.7742	Intermediate Similarity	NPD4694	Approved
0.7742	Intermediate Similarity	NPD5279	Phase 3
0.7742	Intermediate Similarity	NPD5280	Approved
0.7717	Intermediate Similarity	NPD4786	Approved
0.7717	Intermediate Similarity	NPD3666	Approved
0.7717	Intermediate Similarity	NPD3133	Approved
0.7717	Intermediate Similarity	NPD3665	Phase 1
0.7708	Intermediate Similarity	NPD6050	Approved
0.7692	Intermediate Similarity	NPD4269	Approved
0.7692	Intermediate Similarity	NPD4270	Approved
0.7684	Intermediate Similarity	NPD4753	Phase 2
0.767	Intermediate Similarity	NPD7128	Approved
0.767	Intermediate Similarity	NPD6675	Approved
0.767	Intermediate Similarity	NPD5739	Approved
0.767	Intermediate Similarity	NPD6402	Approved
0.7667	Intermediate Similarity	NPD4822	Approved
0.7667	Intermediate Similarity	NPD4821	Approved
0.7667	Intermediate Similarity	NPD4820	Approved
0.7667	Intermediate Similarity	NPD4819	Approved
0.7629	Intermediate Similarity	NPD4202	Approved
0.7619	Intermediate Similarity	NPD6372	Approved
0.7619	Intermediate Similarity	NPD6373	Approved
0.7604	Intermediate Similarity	NPD5692	Phase 3
0.7604	Intermediate Similarity	NPD5207	Approved
0.76	Intermediate Similarity	NPD5696	Approved
0.7582	Intermediate Similarity	NPD5369	Approved
0.7553	Intermediate Similarity	NPD6409	Approved
0.7553	Intermediate Similarity	NPD7146	Approved
0.7553	Intermediate Similarity	NPD6684	Approved
0.7553	Intermediate Similarity	NPD7521	Approved
0.7553	Intermediate Similarity	NPD7334	Approved
0.7553	Intermediate Similarity	NPD5330	Approved
0.7549	Intermediate Similarity	NPD5211	Phase 2
0.7526	Intermediate Similarity	NPD5694	Approved
0.7524	Intermediate Similarity	NPD6899	Approved
0.7524	Intermediate Similarity	NPD6881	Approved
0.7524	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD4221	Approved
0.75	Intermediate Similarity	NPD3667	Approved
0.75	Intermediate Similarity	NPD4755	Approved
0.75	Intermediate Similarity	NPD4223	Phase 3
0.7477	Intermediate Similarity	NPD6650	Approved
0.7477	Intermediate Similarity	NPD6649	Approved
0.7475	Intermediate Similarity	NPD4629	Approved
0.7475	Intermediate Similarity	NPD5210	Approved
0.7473	Intermediate Similarity	NPD4252	Approved
0.7473	Intermediate Similarity	NPD5368	Approved
0.7447	Intermediate Similarity	NPD5363	Approved
0.7447	Intermediate Similarity	NPD5329	Approved
0.7444	Intermediate Similarity	NPD4268	Approved
0.7444	Intermediate Similarity	NPD4271	Approved
0.7429	Intermediate Similarity	NPD5697	Approved
0.7429	Intermediate Similarity	NPD5701	Approved
0.7423	Intermediate Similarity	NPD5785	Approved
0.7419	Intermediate Similarity	NPD5332	Approved
0.7419	Intermediate Similarity	NPD5331	Approved
0.7404	Intermediate Similarity	NPD5141	Approved
0.7396	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6903	Approved
0.7391	Intermediate Similarity	NPD4790	Discontinued
0.7383	Intermediate Similarity	NPD7290	Approved
0.7383	Intermediate Similarity	NPD6883	Approved
0.7383	Intermediate Similarity	NPD7102	Approved
0.7368	Intermediate Similarity	NPD5786	Approved
0.7368	Intermediate Similarity	NPD3618	Phase 1
0.7368	Intermediate Similarity	NPD6098	Approved
0.7368	Intermediate Similarity	NPD5690	Phase 2
0.7358	Intermediate Similarity	NPD6011	Approved
0.7353	Intermediate Similarity	NPD5286	Approved
0.7353	Intermediate Similarity	NPD5285	Approved
0.7353	Intermediate Similarity	NPD4700	Approved
0.7353	Intermediate Similarity	NPD4696	Approved
0.7347	Intermediate Similarity	NPD6411	Approved
0.734	Intermediate Similarity	NPD4197	Approved
0.732	Intermediate Similarity	NPD6904	Approved
0.732	Intermediate Similarity	NPD6080	Approved
0.732	Intermediate Similarity	NPD5328	Approved
0.732	Intermediate Similarity	NPD6673	Approved
0.7315	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6869	Approved
0.7315	Intermediate Similarity	NPD8130	Phase 1
0.7315	Intermediate Similarity	NPD6847	Approved
0.7315	Intermediate Similarity	NPD6617	Approved
0.7312	Intermediate Similarity	NPD6435	Approved
0.73	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6014	Approved
0.729	Intermediate Similarity	NPD6012	Approved
0.729	Intermediate Similarity	NPD6013	Approved
0.7283	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5223	Approved
0.7273	Intermediate Similarity	NPD5779	Approved
0.7273	Intermediate Similarity	NPD5778	Approved
0.7263	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD8297	Approved
0.7248	Intermediate Similarity	NPD6882	Approved
0.7245	Intermediate Similarity	NPD4096	Approved
0.7234	Intermediate Similarity	NPD4788	Approved
0.7216	Intermediate Similarity	NPD6672	Approved
0.7216	Intermediate Similarity	NPD5737	Approved
0.7216	Intermediate Similarity	NPD4518	Approved
0.7212	Intermediate Similarity	NPD5224	Approved
0.7212	Intermediate Similarity	NPD5225	Approved
0.7212	Intermediate Similarity	NPD4633	Approved
0.7212	Intermediate Similarity	NPD5226	Approved
0.7204	Intermediate Similarity	NPD4139	Approved
0.7204	Intermediate Similarity	NPD4692	Approved
0.7191	Intermediate Similarity	NPD6924	Approved
0.7191	Intermediate Similarity	NPD6926	Approved
0.7188	Intermediate Similarity	NPD4688	Approved
0.7188	Intermediate Similarity	NPD4693	Phase 3
0.7188	Intermediate Similarity	NPD4690	Approved
0.7188	Intermediate Similarity	NPD4138	Approved
0.7188	Intermediate Similarity	NPD4689	Approved
0.7188	Intermediate Similarity	NPD5205	Approved
0.7184	Intermediate Similarity	NPD7640	Approved
0.7184	Intermediate Similarity	NPD7639	Approved
0.7184	Intermediate Similarity	NPD6404	Discontinued
0.7172	Intermediate Similarity	NPD8035	Phase 2
0.7172	Intermediate Similarity	NPD8034	Phase 2
0.7172	Intermediate Similarity	NPD7515	Phase 2
0.7172	Intermediate Similarity	NPD6079	Approved
0.7172	Intermediate Similarity	NPD5693	Phase 1
0.7172	Intermediate Similarity	NPD7637	Suspended
0.7158	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD5175	Approved
0.7143	Intermediate Similarity	NPD4754	Approved
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5174	Approved
0.7143	Intermediate Similarity	NPD6051	Approved
0.7129	Intermediate Similarity	NPD5654	Approved
0.71	Intermediate Similarity	NPD5133	Approved
0.7097	Intermediate Similarity	NPD6931	Approved
0.7097	Intermediate Similarity	NPD7525	Registered
0.7097	Intermediate Similarity	NPD6930	Phase 2
0.7091	Intermediate Similarity	NPD6053	Discontinued
0.7087	Intermediate Similarity	NPD7638	Approved
0.7059	Intermediate Similarity	NPD4697	Phase 3
0.7053	Intermediate Similarity	NPD7154	Phase 3
0.7053	Intermediate Similarity	NPD6695	Phase 3
0.7041	Intermediate Similarity	NPD5208	Approved
0.7033	Intermediate Similarity	NPD6933	Approved
0.7033	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4632	Approved
0.701	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4768	Approved
0.7009	Intermediate Similarity	NPD4767	Approved
0.7009	Intermediate Similarity	NPD6008	Approved
0.6991	Remote Similarity	NPD7115	Discovery
0.699	Remote Similarity	NPD7902	Approved
0.699	Remote Similarity	NPD5959	Approved
0.6989	Remote Similarity	NPD6929	Approved
0.6979	Remote Similarity	NPD3668	Phase 3
0.697	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4243	Approved
0.6944	Remote Similarity	NPD6412	Phase 2
0.6939	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6335	Approved
0.6923	Remote Similarity	NPD7339	Approved
0.6923	Remote Similarity	NPD6942	Approved
0.6903	Remote Similarity	NPD6274	Approved
0.6893	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5221	Approved
0.6893	Remote Similarity	NPD5222	Approved
0.6881	Remote Similarity	NPD4729	Approved
0.6881	Remote Similarity	NPD5128	Approved
0.6881	Remote Similarity	NPD4730	Approved
0.687	Remote Similarity	NPD7101	Approved
0.687	Remote Similarity	NPD7100	Approved
0.6863	Remote Similarity	NPD7748	Approved
0.6863	Remote Similarity	NPD6001	Approved
0.6842	Remote Similarity	NPD6317	Approved
0.6842	Remote Similarity	NPD6009	Approved
0.6827	Remote Similarity	NPD5173	Approved
0.6813	Remote Similarity	NPD4784	Approved
0.6813	Remote Similarity	NPD5733	Approved
0.6813	Remote Similarity	NPD4785	Approved
0.6809	Remote Similarity	NPD4195	Approved
0.6783	Remote Similarity	NPD6314	Approved
0.6783	Remote Similarity	NPD6313	Approved
0.6774	Remote Similarity	NPD5776	Phase 2
0.6774	Remote Similarity	NPD6925	Approved
0.6774	Remote Similarity	NPD6116	Phase 1
0.6768	Remote Similarity	NPD4251	Approved
0.6768	Remote Similarity	NPD7750	Discontinued
0.6768	Remote Similarity	NPD4250	Approved
0.6768	Remote Similarity	NPD7524	Approved
0.6757	Remote Similarity	NPD5249	Phase 3
0.6757	Remote Similarity	NPD4634	Approved
0.6757	Remote Similarity	NPD6371	Approved
0.6757	Remote Similarity	NPD5169	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