NPASS Compound

Structure

NPC473565 OpenBabel07101718202D 51 59 0 0 1 0 0 0 0 0999 V2000 -4.2796 -1.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2998 -0.5310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5738 -0.8837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5028 3.1107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3310 2.5816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2223 0.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3500 -0.2924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3431 0.2387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3669 2.1640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1010 0.8337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6852 3.2122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8269 2.7336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6411 0.2642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7827 -0.2144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4680 2.9978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7933 1.9387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9252 -0.6961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6277 2.1662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0238 1.5900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1915 -0.9441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0524 -0.0253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5289 2.7081 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3591 1.3288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9637 1.8765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0336 2.1942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5146 0.0902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1798 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9952 -0.3785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5657 0.8036 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8122 1.7509 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2351 0.5062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5630 0.7267 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9490 0.8939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5483 0.8183 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.9792 0.1341 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4442 1.4078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0351 -0.0106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4588 2.1289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3941 0.6894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6558 1.2469 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9538 1.2723 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5142 1.7255 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9391 0.2897 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0099 0.6042 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0269 1.6767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1402 -0.8354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5391 -0.8543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5136 0.8477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.6140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8420 1.3905 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 2 0 0 0 0 2 20 1 0 0 0 0 4 38 1 0 0 0 0 5 38 1 0 0 0 0 6 39 1 0 0 0 0 7 39 1 0 0 0 0 8 40 1 0 0 0 0 9 41 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 30 1 0 0 0 0 13 14 1 0 0 0 0 13 40 1 0 0 0 0 14 43 1 0 0 0 0 15 22 1 0 0 0 0 15 25 1 0 0 0 0 16 23 2 0 0 0 0 16 24 1 0 0 0 0 17 26 1 0 0 0 0 17 28 1 0 0 0 0 18 27 2 0 0 0 0 18 38 1 0 0 0 0 19 29 1 0 0 0 0 19 41 1 0 0 0 0 21 3 1 1 0 0 0 21 34 1 0 0 0 0 21 37 1 0 0 0 0 22 42 1 6 0 0 0 23 27 1 0 0 0 0 23 31 1 0 0 0 0 24 25 1 0 0 0 0 24 33 2 0 0 0 0 25 36 2 0 0 0 0 26 31 2 0 0 0 0 26 33 1 0 0 0 0 28 20 1 1 0 0 0 28 44 1 0 0 0 0 29 34 1 1 0 0 0 29 50 1 0 0 0 0 30 40 1 1 0 0 0 30 41 1 0 0 0 0 31 35 1 0 0 0 0 32 27 1 6 0 0 0 32 35 1 0 0 0 0 32 39 1 0 0 0 0 33 44 1 0 0 0 0 34 45 1 6 0 0 0 35 46 1 1 0 0 0 36 42 1 0 0 0 0 36 44 1 0 0 0 0 37 47 2 0 0 0 0 37 48 1 0 0 0 0 38 51 1 0 0 0 0 39 51 1 0 0 0 0 40 42 1 6 0 0 0 41 43 1 1 0 0 0 42 10 1 6 0 0 0 43 49 1 6 0 0 0 43 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	699.41
Volume:	729.349
LogP:	7.068
LogD:	4.148
LogS:	-3.574
# Rotatable Bonds:	4
TPSA:	121.38
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	9
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.25
Synthetic Accessibility Score:	6.185
Fsp3:	0.698
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:	-5.468
MDCK Permeability:	2.0264460545149632e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.96
Human Intestinal Absorption (HIA):	0.068
20% Bioavailability (F20%):	0.886
30% Bioavailability (F30%):	0.895

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.685
Plasma Protein Binding (PPB):	93.99532318115234%
Volume Distribution (VD):	1.521
Pgp-substrate:	6.546519756317139%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.972
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.847
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.486
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	9.524
Half-life (T1/2):	0.028

ADMET: Toxicity

hERG Blockers:	0.576
Human Hepatotoxicity (H-HT):	0.61
Drug-inuced Liver Injury (DILI):	0.241
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.067
Carcinogencity:	0.93
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC473565

Natural Product ID:	NPC473565
*Common Name:**	Nodulisporic Acid B2
IUPAC Name:	n.a.
Synonyms:	Nodulisporic Acid B2
Standard InCHIKey:	NAYPRGXEKUQOLV-RUYREXCISA-N
Standard InCHI:	InChI=1S/C43H57NO7/c1-20(2)28-17-26-31-23(27-18-38(4,5)51-39(6,7)32(27)35(31)46)16-24-25-15-22-11-12-30-40(8,42(22,10)36(25)44(28)33(24)26)13-14-43(49)41(30,9)19-29(50-43)34(45)21(3)37(47)48/h16,18,21-22,28-30,32,34-35,45-46,49H,1,11-15,17,19H2,2-10H3,(H,47,48)/t21-,22-,28+,29-,30+,32+,34+,35+,40-,41-,42+,43-/m0/s1
SMILES:	C[C@@H]([C@H]([C@@H]1C[C@@]2([C@](O1)(O)CC[C@]1([C@H]2CC[C@@H]2[C@]1(C)c1n3[C@H](Cc4c3c(c1C2)cc1c4[C@@H](O)[C@H]2C1=CC(OC2(C)C)(C)C)C(=C)C)C)C)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445764
PubChem CID:	44584352
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO32628	nodulisporium	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387649]

☑ 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	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	101.0	nM	PMID[506358]
NPT2523	Organism	Ctenocephalides felis	Ctenocephalides felis	LD90	>	142.9	uM	PMID[506358]

☑ 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 NPC473565 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	372
0.1-0.2	1548
0.2-0.3	3561
0.3-0.4	12987
0.4-0.5	18334
0.5-0.6	4485
0.6-0.7	1280
0.7-0.8	109
0.8-0.85	6
0.85-0.9	8
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9459	High Similarity	NPC473441
0.9459	High Similarity	NPC131273
0.9296	High Similarity	NPC183426
0.9144	High Similarity	NPC311451
0.912	High Similarity	NPC471634
0.912	High Similarity	NPC473806
0.9019	High Similarity	NPC41318
0.9019	High Similarity	NPC469312
0.8919	High Similarity	NPC278540
0.8879	High Similarity	NPC471583
0.8879	High Similarity	NPC471782
0.8636	High Similarity	NPC79107
0.8636	High Similarity	NPC475424
0.8447	Intermediate Similarity	NPC475476
0.8447	Intermediate Similarity	NPC242446
0.8341	Intermediate Similarity	NPC245756
0.8312	Intermediate Similarity	NPC470843
0.8312	Intermediate Similarity	NPC94541
0.8182	Intermediate Similarity	NPC473650
0.8182	Intermediate Similarity	NPC160527
0.7937	Intermediate Similarity	NPC97388
0.7922	Intermediate Similarity	NPC282033
0.7892	Intermediate Similarity	NPC473547
0.7818	Intermediate Similarity	NPC187456
0.7763	Intermediate Similarity	NPC61813
0.7723	Intermediate Similarity	NPC250129
0.7679	Intermediate Similarity	NPC475165
0.7556	Intermediate Similarity	NPC284102
0.7555	Intermediate Similarity	NPC96131
0.7521	Intermediate Similarity	NPC263937
0.7521	Intermediate Similarity	NPC94428
0.7467	Intermediate Similarity	NPC471284
0.7422	Intermediate Similarity	NPC18661
0.738	Intermediate Similarity	NPC235900
0.7354	Intermediate Similarity	NPC475151
0.7269	Intermediate Similarity	NPC470873
0.7265	Intermediate Similarity	NPC102008
0.7265	Intermediate Similarity	NPC473747
0.7179	Intermediate Similarity	NPC162812
0.7175	Intermediate Similarity	NPC231342
0.7161	Intermediate Similarity	NPC470874
0.7149	Intermediate Similarity	NPC107836
0.7137	Intermediate Similarity	NPC123019
0.713	Intermediate Similarity	NPC181502
0.713	Intermediate Similarity	NPC85066
0.7125	Intermediate Similarity	NPC249342
0.7124	Intermediate Similarity	NPC475489
0.7113	Intermediate Similarity	NPC235885
0.7095	Intermediate Similarity	NPC470486
0.7095	Intermediate Similarity	NPC471977
0.7095	Intermediate Similarity	NPC475644
0.7095	Intermediate Similarity	NPC471190
0.708	Intermediate Similarity	NPC32200
0.7069	Intermediate Similarity	NPC234999
0.7064	Intermediate Similarity	NPC30570
0.7059	Intermediate Similarity	NPC34271
0.7054	Intermediate Similarity	NPC475631
0.7054	Intermediate Similarity	NPC87152
0.7054	Intermediate Similarity	NPC228377
0.7054	Intermediate Similarity	NPC475600
0.7054	Intermediate Similarity	NPC477787
0.7054	Intermediate Similarity	NPC122968
0.7054	Intermediate Similarity	NPC476110
0.7054	Intermediate Similarity	NPC328186
0.7049	Intermediate Similarity	NPC237702
0.7045	Intermediate Similarity	NPC253482
0.7045	Intermediate Similarity	NPC237901
0.7045	Intermediate Similarity	NPC195788
0.7037	Intermediate Similarity	NPC473689
0.7037	Intermediate Similarity	NPC292416
0.7012	Intermediate Similarity	NPC472762
0.7012	Intermediate Similarity	NPC473506
0.7009	Intermediate Similarity	NPC292517
0.7009	Intermediate Similarity	NPC475778
0.7008	Intermediate Similarity	NPC30456
0.7008	Intermediate Similarity	NPC319880
0.7008	Intermediate Similarity	NPC244839
0.7008	Intermediate Similarity	NPC320324
0.6992	Remote Similarity	NPC204491
0.6983	Remote Similarity	NPC470280
0.6983	Remote Similarity	NPC211920
0.6971	Remote Similarity	NPC141428
0.6971	Remote Similarity	NPC473850
0.6971	Remote Similarity	NPC475137
0.6971	Remote Similarity	NPC475498
0.6971	Remote Similarity	NPC477902
0.6967	Remote Similarity	NPC475596
0.6967	Remote Similarity	NPC316841
0.6967	Remote Similarity	NPC475303
0.696	Remote Similarity	NPC475648
0.6955	Remote Similarity	NPC475362
0.6953	Remote Similarity	NPC469743
0.6951	Remote Similarity	NPC475406
0.6951	Remote Similarity	NPC170751
0.694	Remote Similarity	NPC260909
0.6937	Remote Similarity	NPC119700
0.693	Remote Similarity	NPC126492
0.6929	Remote Similarity	NPC250807
0.6929	Remote Similarity	NPC76565
0.6929	Remote Similarity	NPC57797
0.6923	Remote Similarity	NPC38959
0.6923	Remote Similarity	NPC327904
0.6917	Remote Similarity	NPC2395
0.6914	Remote Similarity	NPC478080
0.6914	Remote Similarity	NPC146824
0.6914	Remote Similarity	NPC57690
0.6914	Remote Similarity	NPC124029
0.6904	Remote Similarity	NPC301368
0.6904	Remote Similarity	NPC84815
0.6898	Remote Similarity	NPC150698
0.6898	Remote Similarity	NPC96801
0.6888	Remote Similarity	NPC106593
0.6888	Remote Similarity	NPC477788
0.6885	Remote Similarity	NPC1203
0.6883	Remote Similarity	NPC475426
0.6883	Remote Similarity	NPC327769
0.6883	Remote Similarity	NPC35208
0.6875	Remote Similarity	NPC206967
0.687	Remote Similarity	NPC473486
0.687	Remote Similarity	NPC475316
0.6865	Remote Similarity	NPC476090
0.6862	Remote Similarity	NPC294579
0.6862	Remote Similarity	NPC144779
0.686	Remote Similarity	NPC471980
0.6849	Remote Similarity	NPC203614
0.6844	Remote Similarity	NPC472097
0.6842	Remote Similarity	NPC238278
0.6833	Remote Similarity	NPC216428
0.6831	Remote Similarity	NPC313884
0.6831	Remote Similarity	NPC233727
0.6831	Remote Similarity	NPC98371
0.6829	Remote Similarity	NPC470631
0.6829	Remote Similarity	NPC473781
0.6829	Remote Similarity	NPC35390
0.6826	Remote Similarity	NPC195461
0.6826	Remote Similarity	NPC249150
0.6826	Remote Similarity	NPC81654
0.6826	Remote Similarity	NPC49196
0.6826	Remote Similarity	NPC313985
0.6826	Remote Similarity	NPC79129
0.682	Remote Similarity	NPC6981
0.6818	Remote Similarity	NPC127026
0.6818	Remote Similarity	NPC127720
0.681	Remote Similarity	NPC477135
0.6809	Remote Similarity	NPC329982
0.6805	Remote Similarity	NPC140311
0.6802	Remote Similarity	NPC213143
0.6802	Remote Similarity	NPC165201
0.6795	Remote Similarity	NPC475835
0.6793	Remote Similarity	NPC151976
0.6792	Remote Similarity	NPC82070
0.6792	Remote Similarity	NPC62367
0.679	Remote Similarity	NPC473667
0.679	Remote Similarity	NPC147446
0.6784	Remote Similarity	NPC473178
0.6778	Remote Similarity	NPC477907
0.6778	Remote Similarity	NPC42678
0.6778	Remote Similarity	NPC477909
0.6777	Remote Similarity	NPC477903
0.6777	Remote Similarity	NPC472842
0.6772	Remote Similarity	NPC469734
0.677	Remote Similarity	NPC189079
0.6763	Remote Similarity	NPC52254
0.6762	Remote Similarity	NPC328154
0.6761	Remote Similarity	NPC477906
0.6761	Remote Similarity	NPC290529
0.6757	Remote Similarity	NPC472444
0.6756	Remote Similarity	NPC46413
0.675	Remote Similarity	NPC471014
0.675	Remote Similarity	NPC475408
0.675	Remote Similarity	NPC471016
0.6748	Remote Similarity	NPC33949
0.6746	Remote Similarity	NPC37473
0.6742	Remote Similarity	NPC198339
0.6741	Remote Similarity	NPC99428
0.6739	Remote Similarity	NPC50503
0.6736	Remote Similarity	NPC4421
0.6735	Remote Similarity	NPC267926
0.6725	Remote Similarity	NPC205403
0.6723	Remote Similarity	NPC476467
0.6723	Remote Similarity	NPC474905
0.6721	Remote Similarity	NPC475271
0.6721	Remote Similarity	NPC266192
0.6712	Remote Similarity	NPC302191
0.6708	Remote Similarity	NPC470306
0.6708	Remote Similarity	NPC477912
0.6708	Remote Similarity	NPC476114
0.6707	Remote Similarity	NPC285411
0.6707	Remote Similarity	NPC475601
0.6707	Remote Similarity	NPC14116
0.6706	Remote Similarity	NPC472207
0.6697	Remote Similarity	NPC6093
0.6695	Remote Similarity	NPC229348
0.6695	Remote Similarity	NPC162730
0.6695	Remote Similarity	NPC137589
0.6693	Remote Similarity	NPC476516
0.6681	Remote Similarity	NPC214428
0.6681	Remote Similarity	NPC470279
0.6681	Remote Similarity	NPC277350
0.6681	Remote Similarity	NPC204303

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 NPC473565 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	550
0.2-0.3	744
0.3-0.4	2135
0.4-0.5	3515
0.5-0.6	1682
0.6-0.7	273
0.7-0.8	19
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
0.7319	Intermediate Similarity	NPD6995	Phase 1
0.7298	Intermediate Similarity	NPD7769	Phase 3
0.7265	Intermediate Similarity	NPD7778	Approved
0.7265	Intermediate Similarity	NPD7777	Approved
0.7265	Intermediate Similarity	NPD53	Approved
0.7265	Intermediate Similarity	NPD6455	Phase 3
0.7265	Intermediate Similarity	NPD7770	Phase 3
0.725	Intermediate Similarity	NPD7688	Phase 1
0.7234	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8467	Approved
0.7045	Intermediate Similarity	NPD8466	Approved
0.7045	Intermediate Similarity	NPD8465	Approved
0.7045	Intermediate Similarity	NPD8429	Approved
0.7045	Intermediate Similarity	NPD8428	Approved
0.7045	Intermediate Similarity	NPD8427	Approved
0.7011	Intermediate Similarity	NPD8363	Approved
0.7011	Intermediate Similarity	NPD8364	Approved
0.7	Intermediate Similarity	NPD7921	Approved
0.6958	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2920	Discontinued
0.694	Remote Similarity	NPD8460	Approved
0.694	Remote Similarity	NPD8459	Approved
0.694	Remote Similarity	NPD8426	Approved
0.694	Remote Similarity	NPD8425	Approved
0.693	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6978	Phase 2
0.6914	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD8016	Phase 3
0.6875	Remote Similarity	NPD2565	Phase 2
0.6875	Remote Similarity	NPD2564	Approved
0.6858	Remote Similarity	NPD6456	Discontinued
0.6831	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4601	Approved
0.6826	Remote Similarity	NPD4600	Approved
0.6824	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5897	Approved
0.6818	Remote Similarity	NPD5899	Approved
0.6818	Remote Similarity	NPD5898	Approved
0.6792	Remote Similarity	NPD7878	Phase 2
0.6772	Remote Similarity	NPD8468	Phase 2
0.6769	Remote Similarity	NPD5003	Discontinued
0.675	Remote Similarity	NPD8326	Phase 3
0.675	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8325	Phase 3
0.6736	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7707	Approved
0.6726	Remote Similarity	NPD6281	Approved
0.6708	Remote Similarity	NPD5506	Approved
0.6708	Remote Similarity	NPD5507	Approved
0.6681	Remote Similarity	NPD7233	Approved
0.6681	Remote Similarity	NPD7234	Approved
0.6681	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7417	Discontinued
0.6667	Remote Similarity	NPD8489	Phase 1
0.6652	Remote Similarity	NPD6642	Approved
0.6652	Remote Similarity	NPD6641	Approved
0.6625	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7181	Phase 3
0.6614	Remote Similarity	NPD7576	Discontinued
0.6597	Remote Similarity	NPD5835	Phase 3
0.6597	Remote Similarity	NPD5834	Phase 3
0.6587	Remote Similarity	NPD5891	Approved
0.6578	Remote Similarity	NPD7956	Approved
0.6578	Remote Similarity	NPD7955	Approved
0.6573	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD3763	Approved
0.6553	Remote Similarity	NPD7708	Approved
0.655	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5164	Discontinued
0.6542	Remote Similarity	NPD7470	Discontinued
0.654	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.654	Remote Similarity	NPD7957	Phase 1
0.6538	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4897	Phase 2
0.6512	Remote Similarity	NPD5488	Discontinued
0.6498	Remote Similarity	NPD6987	Phase 1
0.6492	Remote Similarity	NPD3925	Approved
0.6491	Remote Similarity	NPD4948	Discontinued
0.6486	Remote Similarity	NPD8358	Approved
0.6477	Remote Similarity	NPD7772	Phase 3
0.6466	Remote Similarity	NPD4602	Approved
0.6459	Remote Similarity	NPD6517	Phase 3
0.6455	Remote Similarity	NPD7803	Approved
0.6454	Remote Similarity	NPD7824	Approved
0.6446	Remote Similarity	NPD7069	Discontinued
0.6444	Remote Similarity	NPD5429	Discontinued
0.6443	Remote Similarity	NPD7791	Approved
0.6443	Remote Similarity	NPD7790	Approved
0.6443	Remote Similarity	NPD7950	Approved
0.6443	Remote Similarity	NPD7952	Approved
0.6443	Remote Similarity	NPD7953	Approved
0.6443	Remote Similarity	NPD7789	Approved
0.6443	Remote Similarity	NPD7951	Approved
0.6429	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7474	Suspended
0.6417	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD8399	Phase 1
0.6417	Remote Similarity	NPD2916	Discontinued
0.6417	Remote Similarity	NPD8423	Phase 2
0.6414	Remote Similarity	NPD7767	Approved
0.6407	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD5936	Approved
0.6405	Remote Similarity	NPD5939	Approved
0.6405	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7001	Phase 3
0.6395	Remote Similarity	NPD6716	Phase 1
0.6395	Remote Similarity	NPD7944	Discontinued
0.6393	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD4334	Discontinued
0.6384	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7946	Pre-registration
0.6375	Remote Similarity	NPD7731	Approved
0.6375	Remote Similarity	NPD7730	Approved
0.6368	Remote Similarity	NPD7418	Discontinued
0.6367	Remote Similarity	NPD8160	Phase 2
0.6364	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.636	Remote Similarity	NPD5901	Discontinued
0.6356	Remote Similarity	NPD6249	Phase 2
0.6356	Remote Similarity	NPD6248	Phase 2
0.6349	Remote Similarity	NPD7780	Approved
0.6349	Remote Similarity	NPD7781	Approved
0.6341	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.634	Remote Similarity	NPD6206	Phase 1
0.6339	Remote Similarity	NPD7797	Approved
0.6339	Remote Similarity	NPD7796	Approved
0.6333	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4427	Phase 2
0.6325	Remote Similarity	NPD4418	Discontinued
0.6324	Remote Similarity	NPD7567	Approved
0.6323	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7395	Discontinued
0.6316	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6314	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6314	Remote Similarity	NPD6261	Phase 3
0.631	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.631	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD4315	Phase 2
0.6307	Remote Similarity	NPD7222	Phase 2
0.6301	Remote Similarity	NPD6733	Discontinued
0.6301	Remote Similarity	NPD7496	Phase 2
0.6301	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6452	Discontinued
0.6295	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD7271	Approved
0.6295	Remote Similarity	NPD6182	Approved
0.6295	Remote Similarity	NPD43	Approved
0.6287	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6999	Discontinued
0.6286	Remote Similarity	NPD8094	Discontinued
0.6271	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4500	Approved
0.6261	Remote Similarity	NPD4501	Approved
0.626	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8101	Phase 3
0.6245	Remote Similarity	NPD8093	Discontinued
0.624	Remote Similarity	NPD7452	Approved
0.624	Remote Similarity	NPD7453	Approved
0.6224	Remote Similarity	NPD8283	Approved
0.6224	Remote Similarity	NPD56	Approved
0.6224	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD8282	Approved
0.6223	Remote Similarity	NPD4499	Approved
0.622	Remote Similarity	NPD3794	Approved
0.622	Remote Similarity	NPD3795	Approved
0.6218	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD2510	Approved
0.6214	Remote Similarity	NPD7666	Phase 3
0.6214	Remote Similarity	NPD7665	Phase 2
0.6214	Remote Similarity	NPD2509	Approved
0.6208	Remote Similarity	NPD6975	Discontinued
0.6205	Remote Similarity	NPD1326	Approved
0.6205	Remote Similarity	NPD1325	Approved
0.6203	Remote Similarity	NPD8357	Approved
0.6198	Remote Similarity	NPD7010	Phase 3
0.6198	Remote Similarity	NPD5530	Phase 1
0.6197	Remote Similarity	NPD5913	Phase 3
0.6197	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6192	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7717	Approved
0.619	Remote Similarity	NPD7716	Approved
0.619	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6189	Remote Similarity	NPD7941	Phase 3
0.6189	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD4373	Phase 2
0.6186	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD5487	Phase 1
0.6181	Remote Similarity	NPD8524	Approved
0.6174	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7962	Phase 2

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