NPASS Compound

Structure

NPC126676 OpenBabel07101718312D 46 51 0 0 1 0 0 0 0 0999 V2000 -9.9181 1.3449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9169 -2.7777 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 -9.6593 0.3789 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 -6.5027 -0.8458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1305 0.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2791 1.5343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2450 1.7932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0203 0.5684 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 -3.8637 -1.0353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1225 -2.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1416 -1.5529 0.0000 C 0 0 0 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 -9.4004 -0.5870 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 -5.5367 -0.5870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4142 1.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0872 1.8625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7615 -1.8117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9522 1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1757 -1.8117 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7956 -1.5529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5708 -0.3282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1213 2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0884 -2.2600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7274 -0.1387 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6390 0.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6933 0.1201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4686 -1.1046 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 -4.3120 0.6378 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8625 3.0872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3473 -3.2259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8978 -0.7765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 2 0 0 0 0 2 27 2 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 9 11 1 0 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 14 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 36 1 0 0 0 0 14 37 1 0 0 0 0 15 16 1 0 0 0 0 15 32 2 0 0 0 0 16 35 2 0 0 0 0 17 19 1 0 0 0 0 17 28 1 0 0 0 0 18 20 1 0 0 0 0 18 29 1 0 0 0 0 19 39 1 0 0 0 0 20 40 1 0 0 0 0 21 30 2 0 0 0 0 21 32 1 0 0 0 0 22 31 2 0 0 0 0 22 33 1 0 0 0 0 23 33 1 0 0 0 0 23 34 2 0 0 0 0 24 30 1 0 0 0 0 24 41 1 0 0 0 0 25 31 1 0 0 0 0 25 42 1 0 0 0 0 26 39 1 0 0 0 0 27 40 1 0 0 0 0 28 41 1 1 0 0 0 29 42 1 1 0 0 0 30 35 1 0 0 0 0 31 38 1 0 0 0 0 32 43 1 0 0 0 0 33 44 2 0 0 0 0 34 38 1 0 0 0 0 34 43 1 0 0 0 0 35 45 1 0 0 0 0 36 39 1 1 0 0 0 36 41 1 0 0 0 0 37 40 1 1 0 0 0 37 42 1 0 0 0 0 38 46 2 0 0 0 0 39 5 1 6 0 0 0 40 6 1 6 0 0 0 41 7 1 1 0 0 0 42 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	623.43
Volume:	697.288
LogP:	7.086
LogD:	5.101
LogS:	-6.897
# Rotatable Bonds:	6
TPSA:	66.4
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	5.301
Fsp3:	0.619
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.091
MDCK Permeability:	6.627607490372611e-06
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.303

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.483
Plasma Protein Binding (PPB):	99.47726440429688%
Volume Distribution (VD):	2.345
Pgp-substrate:	1.1722577810287476%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.491
CYP2C19-inhibitor:	0.263
CYP2C19-substrate:	0.434
CYP2C9-inhibitor:	0.172
CYP2C9-substrate:	0.307
CYP2D6-inhibitor:	0.874
CYP2D6-substrate:	0.815
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.284

ADMET: Excretion

Clearance (CL):	4.7
Half-life (T1/2):	0.116

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.354
Drug-inuced Liver Injury (DILI):	0.246
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.97
Carcinogencity:	0.473
Eye Corrosion:	0.007
Eye Irritation:	0.859
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC126676

Natural Product ID:	NPC126676
*Common Name:**	Popolohuanone A
IUPAC Name:	2-[[(1R,2S,4aR,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]-6-[3-[[(1R,2S,4aR,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]-4-hydroxyanilino]cyclohexa-2,5-diene-1,4-dione
Synonyms:
Standard InCHIKey:	NBPZGPLJHHQVRR-AQQSNAICSA-N
Standard InCHI:	InChI=1S/C42H57NO3/c1-26-11-9-13-36-39(26,5)19-17-28(3)41(36,7)24-30-21-32(15-16-35(30)45)43-34-23-33(44)22-31(38(34)46)25-42(8)29(4)18-20-40(6)27(2)12-10-14-37(40)42/h15-16,21-23,28-29,36-37,43,45H,1-2,9-14,17-20,24-25H2,3-8H3/t28-,29-,36+,37+,39-,40-,41+,42+/m0/s1
SMILES:	C=C1CCC[C@@H]2[C@@]1(C)CC[C@H](C)[C@@]2(C)Cc1cc(ccc1O)NC1=CC(=O)C=C(C[C@]2(C)[C@@H](C)CC[C@@]3(C)C(=C)CCC[C@@H]23)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098249
PubChem CID:	46886871
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002802] Prenylquinones

*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
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374954]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921404]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593283]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18198840]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	at 1020 m depth from Chuuk Atoll, Federated States of Micronesia	n.a.	PMID[18824352]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20230038]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26551342]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26863083]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27336796]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32243140]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[7494145]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748373]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	35000.0	nM	PMID[458564]

☑ 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 NPC126676 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	347
0.1-0.2	1551
0.2-0.3	4978
0.3-0.4	9950
0.4-0.5	17221
0.5-0.6	8073
0.6-0.7	560
0.7-0.8	15
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469671
0.7744	Intermediate Similarity	NPC2672
0.7514	Intermediate Similarity	NPC139506
0.7514	Intermediate Similarity	NPC292143
0.7356	Intermediate Similarity	NPC199737
0.7247	Intermediate Similarity	NPC471778
0.7219	Intermediate Similarity	NPC5630
0.7207	Intermediate Similarity	NPC112336
0.7207	Intermediate Similarity	NPC474814
0.7188	Intermediate Similarity	NPC317727
0.7135	Intermediate Similarity	NPC144691
0.7097	Intermediate Similarity	NPC132751
0.7095	Intermediate Similarity	NPC473484
0.7059	Intermediate Similarity	NPC146370
0.7037	Intermediate Similarity	NPC474059
0.7022	Intermediate Similarity	NPC204867
0.6988	Remote Similarity	NPC316574
0.697	Remote Similarity	NPC475627
0.697	Remote Similarity	NPC475457
0.697	Remote Similarity	NPC475346
0.697	Remote Similarity	NPC18982
0.6968	Remote Similarity	NPC288854
0.6948	Remote Similarity	NPC222982
0.6946	Remote Similarity	NPC298449
0.6943	Remote Similarity	NPC303214
0.6911	Remote Similarity	NPC203628
0.6911	Remote Similarity	NPC70340
0.6905	Remote Similarity	NPC238108
0.6905	Remote Similarity	NPC47986
0.6902	Remote Similarity	NPC471743
0.6894	Remote Similarity	NPC119326
0.6859	Remote Similarity	NPC313293
0.685	Remote Similarity	NPC478075
0.6842	Remote Similarity	NPC323798
0.6839	Remote Similarity	NPC45850
0.6828	Remote Similarity	NPC474815
0.6816	Remote Similarity	NPC93653
0.6805	Remote Similarity	NPC204156
0.6786	Remote Similarity	NPC43353
0.6786	Remote Similarity	NPC477874
0.6786	Remote Similarity	NPC173569
0.6782	Remote Similarity	NPC237649
0.6782	Remote Similarity	NPC300596
0.6776	Remote Similarity	NPC469915
0.677	Remote Similarity	NPC192533
0.6768	Remote Similarity	NPC471489
0.6768	Remote Similarity	NPC232600
0.6766	Remote Similarity	NPC222561
0.6749	Remote Similarity	NPC25961
0.6746	Remote Similarity	NPC249817
0.672	Remote Similarity	NPC470317
0.6719	Remote Similarity	NPC477998
0.6716	Remote Similarity	NPC9894
0.6706	Remote Similarity	NPC198621
0.6706	Remote Similarity	NPC216940
0.6706	Remote Similarity	NPC22676
0.6706	Remote Similarity	NPC475482
0.6667	Remote Similarity	NPC206186
0.6667	Remote Similarity	NPC103250
0.6667	Remote Similarity	NPC470579
0.6649	Remote Similarity	NPC472331
0.6649	Remote Similarity	NPC126515
0.6649	Remote Similarity	NPC274002
0.6647	Remote Similarity	NPC18798
0.6647	Remote Similarity	NPC153007
0.6646	Remote Similarity	NPC154696
0.6632	Remote Similarity	NPC183805
0.6628	Remote Similarity	NPC472241
0.6628	Remote Similarity	NPC470090
0.6616	Remote Similarity	NPC218733
0.6616	Remote Similarity	NPC17677
0.6616	Remote Similarity	NPC265642
0.6616	Remote Similarity	NPC132874
0.6616	Remote Similarity	NPC138615
0.6614	Remote Similarity	NPC298320
0.6611	Remote Similarity	NPC469428
0.6609	Remote Similarity	NPC119569
0.6608	Remote Similarity	NPC181526
0.6608	Remote Similarity	NPC150712
0.6607	Remote Similarity	NPC253476
0.6598	Remote Similarity	NPC106833
0.6598	Remote Similarity	NPC469497
0.659	Remote Similarity	NPC27518
0.659	Remote Similarity	NPC304110
0.659	Remote Similarity	NPC172311
0.6584	Remote Similarity	NPC259703
0.6584	Remote Similarity	NPC32322
0.658	Remote Similarity	NPC21425
0.6579	Remote Similarity	NPC472163
0.6575	Remote Similarity	NPC36495
0.657	Remote Similarity	NPC248287
0.657	Remote Similarity	NPC234548
0.657	Remote Similarity	NPC43477
0.6567	Remote Similarity	NPC475223
0.6567	Remote Similarity	NPC288759
0.6552	Remote Similarity	NPC473804
0.6548	Remote Similarity	NPC149379
0.6546	Remote Similarity	NPC128751
0.6545	Remote Similarity	NPC71610
0.6535	Remote Similarity	NPC246983
0.6535	Remote Similarity	NPC475448
0.6528	Remote Similarity	NPC150308
0.6527	Remote Similarity	NPC117899
0.6527	Remote Similarity	NPC86257
0.6527	Remote Similarity	NPC25736
0.6526	Remote Similarity	NPC283810
0.6522	Remote Similarity	NPC119722
0.6514	Remote Similarity	NPC472242
0.6514	Remote Similarity	NPC477209
0.6514	Remote Similarity	NPC469447
0.6514	Remote Similarity	NPC477873
0.6512	Remote Similarity	NPC472243
0.6512	Remote Similarity	NPC315051
0.6512	Remote Similarity	NPC314252
0.6508	Remote Similarity	NPC477187
0.6506	Remote Similarity	NPC78364
0.6506	Remote Similarity	NPC176130
0.6506	Remote Similarity	NPC84672
0.6506	Remote Similarity	NPC69424
0.6506	Remote Similarity	NPC72667
0.6503	Remote Similarity	NPC475983
0.6502	Remote Similarity	NPC313112
0.6502	Remote Similarity	NPC301292
0.6502	Remote Similarity	NPC133156
0.65	Remote Similarity	NPC114808
0.6494	Remote Similarity	NPC472801
0.6488	Remote Similarity	NPC207873
0.6488	Remote Similarity	NPC90185
0.6488	Remote Similarity	NPC100573
0.648	Remote Similarity	NPC22476
0.6477	Remote Similarity	NPC25491
0.6477	Remote Similarity	NPC49184
0.6467	Remote Similarity	NPC229894
0.6467	Remote Similarity	NPC193203
0.6465	Remote Similarity	NPC21483
0.6465	Remote Similarity	NPC198205
0.6462	Remote Similarity	NPC246700
0.645	Remote Similarity	NPC112752
0.645	Remote Similarity	NPC311054
0.6448	Remote Similarity	NPC27904
0.6446	Remote Similarity	NPC254492
0.6443	Remote Similarity	NPC33902
0.6443	Remote Similarity	NPC276674
0.6441	Remote Similarity	NPC53520
0.6439	Remote Similarity	NPC308943
0.6436	Remote Similarity	NPC472329
0.6436	Remote Similarity	NPC472330
0.6433	Remote Similarity	NPC472262
0.6433	Remote Similarity	NPC287604
0.6433	Remote Similarity	NPC161964
0.6429	Remote Similarity	NPC276238
0.6429	Remote Similarity	NPC171460
0.6425	Remote Similarity	NPC124086
0.6425	Remote Similarity	NPC269449
0.6421	Remote Similarity	NPC256935
0.642	Remote Similarity	NPC190501
0.642	Remote Similarity	NPC318552
0.6418	Remote Similarity	NPC90358
0.6418	Remote Similarity	NPC107828
0.6417	Remote Similarity	NPC314693
0.6416	Remote Similarity	NPC242933
0.6416	Remote Similarity	NPC49911
0.6416	Remote Similarity	NPC277559
0.6413	Remote Similarity	NPC315214
0.6413	Remote Similarity	NPC289776
0.6413	Remote Similarity	NPC191863
0.6413	Remote Similarity	NPC133470
0.6413	Remote Similarity	NPC47298
0.6404	Remote Similarity	NPC1464
0.6402	Remote Similarity	NPC176208
0.64	Remote Similarity	NPC198390
0.6398	Remote Similarity	NPC469727
0.6398	Remote Similarity	NPC126556
0.6398	Remote Similarity	NPC229353
0.6395	Remote Similarity	NPC472804
0.6395	Remote Similarity	NPC477596
0.6392	Remote Similarity	NPC477391
0.6391	Remote Similarity	NPC108129
0.6386	Remote Similarity	NPC137416
0.638	Remote Similarity	NPC103292
0.6379	Remote Similarity	NPC469681
0.6379	Remote Similarity	NPC471974
0.6379	Remote Similarity	NPC469680
0.6378	Remote Similarity	NPC159319
0.6378	Remote Similarity	NPC124626
0.6378	Remote Similarity	NPC32028
0.6369	Remote Similarity	NPC194562
0.6369	Remote Similarity	NPC241392
0.6369	Remote Similarity	NPC96024
0.6369	Remote Similarity	NPC477208
0.6369	Remote Similarity	NPC124802
0.6364	Remote Similarity	NPC198014
0.6364	Remote Similarity	NPC311330
0.6364	Remote Similarity	NPC471187
0.6358	Remote Similarity	NPC126002
0.6358	Remote Similarity	NPC93071
0.6358	Remote Similarity	NPC193358
0.6358	Remote Similarity	NPC474610
0.6358	Remote Similarity	NPC42657
0.6355	Remote Similarity	NPC176371

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 NPC126676 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	237
0.1-0.2	660
0.2-0.3	762
0.3-0.4	1527
0.4-0.5	3679
0.5-0.6	2091
0.6-0.7	186
0.7-0.8	8
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
0.7962	Intermediate Similarity	NPD6636	Phase 3
0.776	Intermediate Similarity	NPD5610	Approved
0.7714	Intermediate Similarity	NPD7324	Discontinued
0.7619	Intermediate Similarity	NPD5086	Approved
0.75	Intermediate Similarity	NPD1913	Phase 1
0.7405	Intermediate Similarity	NPD5928	Phase 1
0.7377	Intermediate Similarity	NPD8167	Discontinued
0.7365	Intermediate Similarity	NPD3141	Discontinued
0.7273	Intermediate Similarity	NPD7301	Phase 3
0.7247	Intermediate Similarity	NPD1839	Phase 1
0.7188	Intermediate Similarity	NPD5608	Approved
0.7188	Intermediate Similarity	NPD5609	Approved
0.7157	Intermediate Similarity	NPD7300	Phase 3
0.7157	Intermediate Similarity	NPD7302	Phase 3
0.7143	Intermediate Similarity	NPD5937	Approved
0.7127	Intermediate Similarity	NPD7449	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7293	Approved
0.7083	Intermediate Similarity	NPD1625	Approved
0.7076	Intermediate Similarity	NPD4888	Discontinued
0.7047	Intermediate Similarity	NPD5197	Approved
0.7047	Intermediate Similarity	NPD5196	Approved
0.7047	Intermediate Similarity	NPD5194	Approved
0.7027	Intermediate Similarity	NPD5637	Discontinued
0.7011	Intermediate Similarity	NPD3229	Phase 2
0.6995	Remote Similarity	NPD5195	Discontinued
0.6989	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD9279	Approved
0.6982	Remote Similarity	NPD7082	Approved
0.6941	Remote Similarity	NPD7259	Approved
0.6932	Remote Similarity	NPD2672	Discontinued
0.6915	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6162	Approved
0.6907	Remote Similarity	NPD6161	Approved
0.6901	Remote Similarity	NPD8131	Suspended
0.6901	Remote Similarity	NPD7295	Approved
0.6865	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1626	Approved
0.6842	Remote Similarity	NPD1196	Approved
0.6828	Remote Similarity	NPD7479	Phase 2
0.6821	Remote Similarity	NPD1543	Discontinued
0.6811	Remote Similarity	NPD2361	Approved
0.6805	Remote Similarity	NPD3391	Approved
0.6796	Remote Similarity	NPD1168	Approved
0.6791	Remote Similarity	NPD5445	Approved
0.6791	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD1195	Approved
0.678	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7292	Approved
0.6757	Remote Similarity	NPD2359	Approved
0.6757	Remote Similarity	NPD5466	Approved
0.675	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1189	Approved
0.672	Remote Similarity	NPD1544	Phase 1
0.6701	Remote Similarity	NPD4668	Phase 2
0.67	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6376	Discontinued
0.6649	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7487	Discontinued
0.6612	Remote Similarity	NPD5430	Discontinued
0.6599	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5810	Discontinued
0.6596	Remote Similarity	NPD5498	Phase 2
0.6595	Remote Similarity	NPD1161	Approved
0.659	Remote Similarity	NPD4430	Phase 2
0.6587	Remote Similarity	NPD8149	Discontinued
0.6584	Remote Similarity	NPD6250	Discontinued
0.6578	Remote Similarity	NPD5033	Approved
0.6576	Remote Similarity	NPD5823	Approved
0.6575	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6283	Phase 2
0.6571	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD2916	Discontinued
0.6557	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2789	Approved
0.6552	Remote Similarity	NPD8166	Discontinued
0.6552	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.655	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5599	Discontinued
0.6534	Remote Similarity	NPD7478	Approved
0.6531	Remote Similarity	NPD7570	Approved
0.6531	Remote Similarity	NPD7569	Approved
0.6508	Remote Similarity	NPD1170	Approved
0.6505	Remote Similarity	NPD5186	Approved
0.6505	Remote Similarity	NPD5183	Approved
0.6497	Remote Similarity	NPD4161	Discontinued
0.6482	Remote Similarity	NPD6527	Approved
0.6477	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4956	Approved
0.6471	Remote Similarity	NPD3776	Discontinued
0.6471	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD3453	Discontinued
0.6462	Remote Similarity	NPD6835	Approved
0.6461	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7883	Discontinued
0.6458	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6457	Approved
0.6443	Remote Similarity	NPD3153	Approved
0.6443	Remote Similarity	NPD3154	Approved
0.644	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7476	Discontinued
0.6436	Remote Similarity	NPD7854	Phase 2
0.6425	Remote Similarity	NPD7606	Phase 3
0.6422	Remote Similarity	NPD4465	Phase 2
0.6422	Remote Similarity	NPD1294	Discontinued
0.6422	Remote Similarity	NPD4467	Phase 2
0.642	Remote Similarity	NPD3019	Approved
0.642	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.642	Remote Similarity	NPD2932	Approved
0.6414	Remote Similarity	NPD7262	Phase 1
0.6413	Remote Similarity	NPD1684	Approved
0.6413	Remote Similarity	NPD1685	Approved
0.6408	Remote Similarity	NPD4859	Phase 1
0.6406	Remote Similarity	NPD5039	Approved
0.6402	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD7283	Approved
0.6396	Remote Similarity	NPD5871	Discontinued
0.6395	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.639	Remote Similarity	NPD6807	Phase 3
0.6383	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD3975	Discontinued
0.638	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD2791	Discontinued
0.6373	Remote Similarity	NPD7962	Phase 2
0.6369	Remote Similarity	NPD2606	Approved
0.6369	Remote Similarity	NPD3595	Approved
0.6369	Remote Similarity	NPD3594	Approved
0.6369	Remote Similarity	NPD2605	Approved
0.6364	Remote Similarity	NPD5819	Phase 2
0.6354	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5997	Discontinued
0.6345	Remote Similarity	NPD4258	Approved
0.6345	Remote Similarity	NPD4259	Approved
0.6344	Remote Similarity	NPD3252	Approved
0.6343	Remote Similarity	NPD9277	Approved
0.6343	Remote Similarity	NPD75	Approved
0.634	Remote Similarity	NPD7546	Discontinued
0.6339	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD3784	Discontinued
0.6337	Remote Similarity	NPD6874	Approved
0.6335	Remote Similarity	NPD3755	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1230	Approved
0.6332	Remote Similarity	NPD6526	Approved
0.6331	Remote Similarity	NPD5156	Approved
0.6331	Remote Similarity	NPD5155	Approved
0.6327	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6483	Approved
0.6327	Remote Similarity	NPD6484	Approved
0.6325	Remote Similarity	NPD6320	Approved
0.6319	Remote Similarity	NPD3684	Discontinued
0.6318	Remote Similarity	NPD4423	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3636	Approved
0.631	Remote Similarity	NPD3635	Approved
0.631	Remote Similarity	NPD3637	Approved
0.631	Remote Similarity	NPD3251	Approved
0.6308	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD2820	Phase 3
0.6306	Remote Similarity	NPD9376	Approved
0.6301	Remote Similarity	NPD6342	Discontinued
0.63	Remote Similarity	NPD7256	Discontinued
0.6294	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7922	Phase 1
0.6289	Remote Similarity	NPD5032	Approved
0.6289	Remote Similarity	NPD8281	Discontinued
0.6286	Remote Similarity	NPD9276	Approved
0.6286	Remote Similarity	NPD9275	Approved
0.6286	Remote Similarity	NPD9278	Suspended
0.6286	Remote Similarity	NPD9274	Approved
0.6284	Remote Similarity	NPD2366	Approved
0.6284	Remote Similarity	NPD2836	Approved
0.6275	Remote Similarity	NPD6321	Discontinued
0.6274	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7003	Approved
0.6265	Remote Similarity	NPD1755	Approved
0.6263	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7654	Discontinued
0.6256	Remote Similarity	NPD5035	Approved
0.625	Remote Similarity	NPD4256	Phase 2
0.625	Remote Similarity	NPD4539	Phase 1
0.625	Remote Similarity	NPD2365	Approved
0.625	Remote Similarity	NPD8311	Discontinued
0.625	Remote Similarity	NPD4257	Approved
0.6244	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7316	Discontinued
0.6244	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD2369	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data