NPASS Compound

Structure

NPC183426 OpenBabel07101719152D 50 58 0 0 1 0 0 0 0 0999 V2000 -4.2783 -1.9224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2988 -0.5309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5224 2.5195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4999 3.1097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3279 2.5808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2192 0.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3471 -0.2923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3418 0.2387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3665 2.1634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1001 0.8335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6844 3.2112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8263 2.7327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6403 0.2641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7822 -0.2143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5479 0.8181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4666 2.9969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7912 1.9381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9233 -0.6959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0238 1.5895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6250 2.1655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1902 -0.9439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0263 1.6762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5278 2.7073 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5655 0.8034 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3568 1.3284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9618 1.8759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0321 2.1935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5126 0.0902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1773 1.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9936 -0.3783 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8116 1.7504 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2329 0.5061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5604 0.7265 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9471 0.8936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9767 0.1340 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4428 1.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0087 1.6909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4558 2.1282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3912 0.6892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6550 1.2465 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9535 1.2719 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5131 1.7249 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9388 0.2896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0083 0.6040 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.1377 -0.8351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4871 2.5489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5126 0.8475 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3249 -0.6138 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 -9.8389 1.3901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 2 0 0 0 0 2 21 1 0 0 0 0 3 22 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 23 1 0 0 0 0 12 31 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 2 0 0 0 0 16 23 1 0 0 0 0 16 27 1 0 0 0 0 17 25 2 0 0 0 0 17 26 1 0 0 0 0 18 28 1 0 0 0 0 18 30 1 0 0 0 0 19 24 1 0 0 0 0 19 41 1 0 0 0 0 20 29 2 0 0 0 0 20 38 1 0 0 0 0 22 37 1 0 0 0 0 23 42 1 6 0 0 0 24 15 1 1 0 0 0 24 49 1 0 0 0 0 25 29 1 0 0 0 0 25 32 1 0 0 0 0 26 27 1 0 0 0 0 26 34 2 0 0 0 0 27 36 2 0 0 0 0 28 32 2 0 0 0 0 28 34 1 0 0 0 0 30 21 1 1 0 0 0 30 44 1 0 0 0 0 31 40 1 1 0 0 0 31 41 1 0 0 0 0 32 35 1 0 0 0 0 33 29 1 6 0 0 0 33 35 1 0 0 0 0 33 39 1 0 0 0 0 34 44 1 0 0 0 0 35 45 1 1 0 0 0 36 42 1 0 0 0 0 36 44 1 0 0 0 0 37 46 2 0 0 0 0 37 47 1 0 0 0 0 38 50 1 0 0 0 0 39 50 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 48 1 6 0 0 0 43 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	681.4
Volume:	717.922
LogP:	7.667
LogD:	4.581
LogS:	-3.04
# Rotatable Bonds:	3
TPSA:	101.15
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	9
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.282
Synthetic Accessibility Score:	6.137
Fsp3:	0.651
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:	-5.462
MDCK Permeability:	2.5453689886489883e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.772
Human Intestinal Absorption (HIA):	0.155
20% Bioavailability (F20%):	0.932
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.721
Plasma Protein Binding (PPB):	95.3006820678711%
Volume Distribution (VD):	1.69
Pgp-substrate:	4.373581409454346%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.918
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.827
CYP2C9-inhibitor:	0.255
CYP2C9-substrate:	0.126
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.606
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	8.762
Half-life (T1/2):	0.027

ADMET: Toxicity

hERG Blockers:	0.72
Human Hepatotoxicity (H-HT):	0.852
Drug-inuced Liver Injury (DILI):	0.076
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.95
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.385
Carcinogencity:	0.927
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC183426

Natural Product ID:	NPC183426
*Common Name:**	Nodulisporic Acid B1
IUPAC Name:	n.a.
Synonyms:	Nodulisporic Acid B1
Standard InCHIKey:	PLSGFSOLCKJLJQ-KHJKSYPCSA-N
Standard InCHI:	InChI=1S/C43H55NO6/c1-21(2)30-18-28-32-25(29-20-38(4,5)50-39(6,7)33(29)35(32)45)17-26-27-16-23-11-12-31-40(8,42(23,10)36(27)44(30)34(26)28)13-14-43(48)41(31,9)19-24(49-43)15-22(3)37(46)47/h15,17,20,23-24,30-31,33,35,45,48H,1,11-14,16,18-19H2,2-10H3,(H,46,47)/b22-15+/t23-,24+,30+,31+,33+,35+,40-,41-,42+,43-/m0/s1
SMILES:	C/C(=C[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)/C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444440
PubChem CID:	44331197
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	=	121.0	nM	PMID[458526]
NPT2523	Organism	Ctenocephalides felis	Ctenocephalides felis	LD90	>	147.7	uM	PMID[458526]

☑ 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 NPC183426 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	387
0.1-0.2	1528
0.2-0.3	4001
0.3-0.4	16781
0.4-0.5	14761
0.5-0.6	3907
0.6-0.7	1245
0.7-0.8	63
0.8-0.85	6
0.85-0.9	10
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9703	High Similarity	NPC469312
0.9703	High Similarity	NPC41318
0.9349	High Similarity	NPC311451
0.9296	High Similarity	NPC473565
0.9116	High Similarity	NPC278540
0.9082	High Similarity	NPC475476
0.9082	High Similarity	NPC242446
0.9074	High Similarity	NPC471782
0.9074	High Similarity	NPC471583
0.8969	High Similarity	NPC131273
0.8969	High Similarity	NPC473441
0.8798	High Similarity	NPC160527
0.8798	High Similarity	NPC473650
0.8605	High Similarity	NPC245756
0.8531	High Similarity	NPC97388
0.8483	Intermediate Similarity	NPC473547
0.8447	Intermediate Similarity	NPC473806
0.8447	Intermediate Similarity	NPC471634
0.8413	Intermediate Similarity	NPC187456
0.8302	Intermediate Similarity	NPC250129
0.8255	Intermediate Similarity	NPC475165
0.8238	Intermediate Similarity	NPC94541
0.8238	Intermediate Similarity	NPC470843
0.7982	Intermediate Similarity	NPC79107
0.7982	Intermediate Similarity	NPC475424
0.7915	Intermediate Similarity	NPC475151
0.7841	Intermediate Similarity	NPC282033
0.782	Intermediate Similarity	NPC473747
0.7788	Intermediate Similarity	NPC284102
0.76	Intermediate Similarity	NPC61813
0.7406	Intermediate Similarity	NPC206967
0.7389	Intermediate Similarity	NPC96131
0.7288	Intermediate Similarity	NPC263937
0.7288	Intermediate Similarity	NPC94428
0.7233	Intermediate Similarity	NPC126492
0.7225	Intermediate Similarity	NPC471284
0.7212	Intermediate Similarity	NPC235900
0.7179	Intermediate Similarity	NPC470873
0.7136	Intermediate Similarity	NPC32200
0.7117	Intermediate Similarity	NPC123019
0.7116	Intermediate Similarity	NPC34271
0.7111	Intermediate Similarity	NPC470280
0.7094	Intermediate Similarity	NPC235885
0.7078	Intermediate Similarity	NPC231342
0.7069	Intermediate Similarity	NPC470874
0.7064	Intermediate Similarity	NPC473178
0.7034	Intermediate Similarity	NPC249342
0.7028	Intermediate Similarity	NPC198339
0.6991	Remote Similarity	NPC119700
0.6981	Remote Similarity	NPC6093
0.6955	Remote Similarity	NPC181502
0.6955	Remote Similarity	NPC85066
0.6949	Remote Similarity	NPC313884
0.6949	Remote Similarity	NPC98371
0.6937	Remote Similarity	NPC102008
0.6933	Remote Similarity	NPC470486
0.6933	Remote Similarity	NPC471190
0.6933	Remote Similarity	NPC475644
0.6933	Remote Similarity	NPC471977
0.6933	Remote Similarity	NPC477135
0.6894	Remote Similarity	NPC2395
0.6891	Remote Similarity	NPC475631
0.6891	Remote Similarity	NPC328186
0.6891	Remote Similarity	NPC87152
0.6891	Remote Similarity	NPC228377
0.6891	Remote Similarity	NPC475600
0.6891	Remote Similarity	NPC122968
0.6891	Remote Similarity	NPC476110
0.6891	Remote Similarity	NPC477787
0.6888	Remote Similarity	NPC237702
0.6883	Remote Similarity	NPC469734
0.6881	Remote Similarity	NPC46413
0.6875	Remote Similarity	NPC292416
0.6875	Remote Similarity	NPC473689
0.6872	Remote Similarity	NPC18661
0.6855	Remote Similarity	NPC107836
0.6853	Remote Similarity	NPC329982
0.6852	Remote Similarity	NPC165201
0.6849	Remote Similarity	NPC473506
0.6847	Remote Similarity	NPC205403
0.6846	Remote Similarity	NPC244839
0.6846	Remote Similarity	NPC320324
0.6846	Remote Similarity	NPC30456
0.6846	Remote Similarity	NPC319880
0.6838	Remote Similarity	NPC294579
0.6838	Remote Similarity	NPC144779
0.6837	Remote Similarity	NPC302191
0.6835	Remote Similarity	NPC473177
0.6826	Remote Similarity	NPC475422
0.6826	Remote Similarity	NPC234999
0.6824	Remote Similarity	NPC203614
0.6824	Remote Similarity	NPC204491
0.6807	Remote Similarity	NPC473850
0.6807	Remote Similarity	NPC475137
0.6807	Remote Similarity	NPC475498
0.6806	Remote Similarity	NPC472444
0.6806	Remote Similarity	NPC19679
0.6805	Remote Similarity	NPC475303
0.6805	Remote Similarity	NPC475596
0.6805	Remote Similarity	NPC316841
0.68	Remote Similarity	NPC470279
0.6795	Remote Similarity	NPC6981
0.6793	Remote Similarity	NPC477788
0.6792	Remote Similarity	NPC475362
0.6792	Remote Similarity	NPC97525
0.679	Remote Similarity	NPC475406
0.679	Remote Similarity	NPC170751
0.6778	Remote Similarity	NPC472762
0.6774	Remote Similarity	NPC476090
0.6767	Remote Similarity	NPC475778
0.6765	Remote Similarity	NPC76565
0.6765	Remote Similarity	NPC250807
0.6765	Remote Similarity	NPC57797
0.6762	Remote Similarity	NPC327904
0.6762	Remote Similarity	NPC38959
0.6759	Remote Similarity	NPC478080
0.675	Remote Similarity	NPC146824
0.675	Remote Similarity	NPC57690
0.6744	Remote Similarity	NPC472443
0.6739	Remote Similarity	NPC87755
0.6737	Remote Similarity	NPC301368
0.6737	Remote Similarity	NPC84815
0.6729	Remote Similarity	NPC56618
0.6726	Remote Similarity	NPC475489
0.6723	Remote Similarity	NPC162812
0.6721	Remote Similarity	NPC327769
0.6721	Remote Similarity	NPC37473
0.671	Remote Similarity	NPC469743
0.6708	Remote Similarity	NPC475316
0.6708	Remote Similarity	NPC473486
0.6696	Remote Similarity	NPC475835
0.6695	Remote Similarity	NPC147446
0.6695	Remote Similarity	NPC471980
0.6682	Remote Similarity	NPC472586
0.6682	Remote Similarity	NPC192306
0.6681	Remote Similarity	NPC126066
0.668	Remote Similarity	NPC253482
0.668	Remote Similarity	NPC285411
0.668	Remote Similarity	NPC70155
0.668	Remote Similarity	NPC14116
0.6667	Remote Similarity	NPC216428
0.6667	Remote Similarity	NPC271215
0.6667	Remote Similarity	NPC473781
0.6667	Remote Similarity	NPC137589
0.6667	Remote Similarity	NPC46451
0.6667	Remote Similarity	NPC141428
0.6667	Remote Similarity	NPC477531
0.6667	Remote Similarity	NPC470631
0.6667	Remote Similarity	NPC149471
0.6667	Remote Similarity	NPC193761
0.6667	Remote Similarity	NPC475602
0.6667	Remote Similarity	NPC35390
0.6653	Remote Similarity	NPC314552
0.6653	Remote Similarity	NPC475408
0.6653	Remote Similarity	NPC127720
0.6653	Remote Similarity	NPC311196
0.6653	Remote Similarity	NPC252251
0.6653	Remote Similarity	NPC471014
0.6653	Remote Similarity	NPC106593
0.6653	Remote Similarity	NPC127026
0.6653	Remote Similarity	NPC134384
0.6652	Remote Similarity	NPC249150
0.6652	Remote Similarity	NPC79129
0.6652	Remote Similarity	NPC81654
0.6652	Remote Similarity	NPC195461
0.6652	Remote Similarity	NPC49196
0.6652	Remote Similarity	NPC313985
0.6642	Remote Similarity	NPC195788
0.6642	Remote Similarity	NPC237901
0.6639	Remote Similarity	NPC477533
0.6639	Remote Similarity	NPC202503
0.6639	Remote Similarity	NPC140311
0.6639	Remote Similarity	NPC132642
0.6638	Remote Similarity	NPC4421
0.6627	Remote Similarity	NPC473540
0.6626	Remote Similarity	NPC209174
0.6625	Remote Similarity	NPC473667
0.6624	Remote Similarity	NPC62367
0.6624	Remote Similarity	NPC87856
0.6624	Remote Similarity	NPC23614
0.6624	Remote Similarity	NPC100079
0.6624	Remote Similarity	NPC204446
0.6624	Remote Similarity	NPC151976
0.662	Remote Similarity	NPC211997
0.6614	Remote Similarity	NPC189079
0.6612	Remote Similarity	NPC211920
0.6612	Remote Similarity	NPC470126
0.661	Remote Similarity	NPC477909
0.661	Remote Similarity	NPC30570
0.661	Remote Similarity	NPC470306
0.661	Remote Similarity	NPC42678
0.661	Remote Similarity	NPC132211
0.661	Remote Similarity	NPC477907
0.6602	Remote Similarity	NPC1203
0.66	Remote Similarity	NPC475648
0.6598	Remote Similarity	NPC477902
0.6598	Remote Similarity	NPC328154
0.6596	Remote Similarity	NPC267965
0.6595	Remote Similarity	NPC470931
0.6592	Remote Similarity	NPC472097

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 NPC183426 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	588
0.2-0.3	667
0.3-0.4	2056
0.4-0.5	3548
0.5-0.6	1747
0.6-0.7	317
0.7-0.8	7
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
0.7456	Intermediate Similarity	NPD6995	Phase 1
0.7382	Intermediate Similarity	NPD7688	Phase 1
0.7325	Intermediate Similarity	NPD6455	Phase 3
0.7293	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7770	Phase 3
0.7073	Intermediate Similarity	NPD7769	Phase 3
0.7049	Intermediate Similarity	NPD7921	Approved
0.7034	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6978	Phase 2
0.7005	Intermediate Similarity	NPD6281	Approved
0.7004	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7778	Approved
0.6937	Remote Similarity	NPD53	Approved
0.6937	Remote Similarity	NPD7777	Approved
0.6906	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5891	Approved
0.6889	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8016	Phase 3
0.6853	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD8364	Approved
0.6795	Remote Similarity	NPD8363	Approved
0.6784	Remote Similarity	NPD2920	Discontinued
0.675	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7417	Discontinued
0.6709	Remote Similarity	NPD7707	Approved
0.6698	Remote Similarity	NPD7474	Suspended
0.6697	Remote Similarity	NPD2564	Approved
0.6697	Remote Similarity	NPD2565	Phase 2
0.6682	Remote Similarity	NPD4948	Discontinued
0.6681	Remote Similarity	NPD5506	Approved
0.6681	Remote Similarity	NPD5507	Approved
0.6681	Remote Similarity	NPD6987	Phase 1
0.6667	Remote Similarity	NPD3763	Approved
0.6667	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD5164	Discontinued
0.6652	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4600	Approved
0.6652	Remote Similarity	NPD7957	Phase 1
0.6652	Remote Similarity	NPD4601	Approved
0.6651	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD8465	Approved
0.6642	Remote Similarity	NPD8428	Approved
0.6642	Remote Similarity	NPD8429	Approved
0.6642	Remote Similarity	NPD8466	Approved
0.6642	Remote Similarity	NPD8467	Approved
0.6642	Remote Similarity	NPD8427	Approved
0.6637	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7418	Discontinued
0.6624	Remote Similarity	NPD7878	Phase 2
0.6614	Remote Similarity	NPD8468	Phase 2
0.6609	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5003	Discontinued
0.6584	Remote Similarity	NPD7767	Approved
0.658	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD4418	Discontinued
0.6577	Remote Similarity	NPD6456	Discontinued
0.6577	Remote Similarity	NPD7233	Approved
0.6577	Remote Similarity	NPD7234	Approved
0.6567	Remote Similarity	NPD5835	Phase 3
0.6567	Remote Similarity	NPD5834	Phase 3
0.656	Remote Similarity	NPD5898	Approved
0.656	Remote Similarity	NPD5899	Approved
0.656	Remote Similarity	NPD5897	Approved
0.656	Remote Similarity	NPD6452	Discontinued
0.6557	Remote Similarity	NPD7567	Approved
0.6557	Remote Similarity	NPD7824	Approved
0.6552	Remote Similarity	NPD7222	Phase 2
0.6548	Remote Similarity	NPD5488	Discontinued
0.6543	Remote Similarity	NPD8460	Approved
0.6543	Remote Similarity	NPD8459	Approved
0.6543	Remote Similarity	NPD8425	Approved
0.6543	Remote Similarity	NPD8426	Approved
0.6537	Remote Similarity	NPD5901	Discontinued
0.6518	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD5936	Approved
0.6511	Remote Similarity	NPD7470	Discontinued
0.6511	Remote Similarity	NPD5939	Approved
0.6509	Remote Similarity	NPD7001	Phase 3
0.6502	Remote Similarity	NPD4334	Discontinued
0.6498	Remote Similarity	NPD4897	Phase 2
0.6485	Remote Similarity	NPD7395	Discontinued
0.6481	Remote Similarity	NPD7452	Approved
0.6481	Remote Similarity	NPD7453	Approved
0.6475	Remote Similarity	NPD7730	Approved
0.6475	Remote Similarity	NPD7731	Approved
0.6471	Remote Similarity	NPD8160	Phase 2
0.6466	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD1326	Approved
0.6465	Remote Similarity	NPD1325	Approved
0.6461	Remote Similarity	NPD7271	Approved
0.6457	Remote Similarity	NPD8358	Approved
0.6456	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD7576	Discontinued
0.6445	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5913	Phase 3
0.6441	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD5530	Phase 1
0.6429	Remote Similarity	NPD6716	Phase 1
0.6426	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5104	Approved
0.6419	Remote Similarity	NPD4640	Approved
0.6419	Remote Similarity	NPD4638	Approved
0.6419	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD4639	Approved
0.6416	Remote Similarity	NPD4315	Phase 2
0.6414	Remote Similarity	NPD7069	Discontinued
0.6411	Remote Similarity	NPD7953	Approved
0.6411	Remote Similarity	NPD7790	Approved
0.6411	Remote Similarity	NPD7950	Approved
0.6411	Remote Similarity	NPD7951	Approved
0.6411	Remote Similarity	NPD7791	Approved
0.6411	Remote Similarity	NPD7952	Approved
0.6411	Remote Similarity	NPD7789	Approved
0.641	Remote Similarity	NPD5429	Discontinued
0.6408	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD7181	Phase 3
0.6402	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6733	Discontinued
0.6395	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6642	Approved
0.6393	Remote Similarity	NPD3925	Approved
0.6393	Remote Similarity	NPD6641	Approved
0.6391	Remote Similarity	NPD6999	Discontinued
0.6391	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD2916	Discontinued
0.6383	Remote Similarity	NPD2510	Approved
0.6383	Remote Similarity	NPD2509	Approved
0.6382	Remote Similarity	NPD7555	Discontinued
0.6372	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7010	Phase 3
0.636	Remote Similarity	NPD7944	Discontinued
0.636	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.636	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7962	Phase 2
0.6349	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7946	Pre-registration
0.6343	Remote Similarity	NPD5021	Discontinued
0.6327	Remote Similarity	NPD8063	Discontinued
0.6325	Remote Similarity	NPD56	Approved
0.6325	Remote Similarity	NPD8283	Approved
0.6325	Remote Similarity	NPD8282	Approved
0.632	Remote Similarity	NPD6249	Phase 2
0.632	Remote Similarity	NPD6248	Phase 2
0.6316	Remote Similarity	NPD7781	Approved
0.6316	Remote Similarity	NPD7780	Approved
0.6314	Remote Similarity	NPD8399	Phase 1
0.6314	Remote Similarity	NPD7665	Phase 2
0.6314	Remote Similarity	NPD7671	Approved
0.6314	Remote Similarity	NPD8423	Phase 2
0.6314	Remote Similarity	NPD7666	Phase 3
0.6314	Remote Similarity	NPD7672	Approved
0.6311	Remote Similarity	NPD2383	Phase 1
0.6309	Remote Similarity	NPD6975	Discontinued
0.6305	Remote Similarity	NPD7797	Approved
0.6305	Remote Similarity	NPD7796	Approved
0.6304	Remote Similarity	NPD6206	Phase 1
0.6298	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD7955	Approved
0.6298	Remote Similarity	NPD7956	Approved
0.6295	Remote Similarity	NPD5075	Discontinued
0.6293	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.629	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6158	Phase 2
0.6286	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD8489	Phase 1
0.6286	Remote Similarity	NPD7717	Approved
0.6286	Remote Similarity	NPD7716	Approved
0.628	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6635	Approved
0.6278	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6261	Phase 3
0.6274	Remote Similarity	NPD7708	Approved
0.6273	Remote Similarity	NPD5100	Phase 3
0.6261	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7935	Phase 2
0.6261	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7776	Approved
0.626	Remote Similarity	NPD7772	Phase 3
0.6255	Remote Similarity	NPD3947	Discontinued
0.625	Remote Similarity	NPD2915	Discontinued
0.625	Remote Similarity	NPD8094	Discontinued
0.6239	Remote Similarity	NPD8021	Approved
0.6239	Remote Similarity	NPD8431	Approved
0.6239	Remote Similarity	NPD8020	Approved
0.6235	Remote Similarity	NPD7856	Phase 2
0.6235	Remote Similarity	NPD6517	Phase 3
0.6235	Remote Similarity	NPD7857	Phase 3
0.6234	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7678	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