NPASS Compound

Structure

CID162812 OpenBabel06191715532D 37 43 0 0 1 0 0 0 0 0999 V2000 -0.0453 -1.1377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5044 3.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9933 1.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9536 1.3895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4551 2.3618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5010 2.3618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7799 -1.1850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6881 -0.6607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6881 2.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7799 1.9611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5045 0.3882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4125 0.9125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9322 1.5355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5926 0.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5010 0.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9671 1.5547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8717 -0.6606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0239 1.5355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0697 1.5355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6385 0.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5964 1.9611 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6881 0.3881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1614 1.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7720 1.3370 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6384 2.3618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5044 2.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7799 0.9124 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5963 0.9124 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4126 1.9610 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8717 0.3881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4552 0.7091 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1902 2.6140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1613 3.1881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2594 2.4500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6710 1.9611 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5926 2.3618 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 1 17 1 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 17 2 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 27 1 0 0 0 0 11 12 1 0 0 0 0 12 29 1 0 0 0 0 13 31 2 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 15 18 2 0 0 0 0 15 31 1 0 0 0 0 16 28 1 0 0 0 0 16 35 1 0 0 0 0 18 19 1 0 0 0 0 19 36 1 0 0 0 0 20 23 2 0 0 0 0 20 37 1 0 0 0 0 21 26 1 0 0 0 0 21 28 1 6 0 0 0 22 27 1 6 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 24 30 1 1 0 0 0 24 32 1 0 0 0 0 25 33 2 0 0 0 0 25 36 1 0 0 0 0 26 29 1 0 0 0 0 27 30 1 1 0 0 0 28 11 1 1 0 0 0 29 34 1 6 0 0 0 29 35 1 0 0 0 0 30 17 1 6 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	505.25
Volume:	512.824
LogP:	3.648
LogD:	3.295
LogS:	-4.348
# Rotatable Bonds:	1
TPSA:	102.02
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.538
Synthetic Accessibility Score:	6.425
Fsp3:	0.6
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:	-5.06
MDCK Permeability:	1.680660898273345e-05
Pgp-inhibitor:	0.247
Pgp-substrate:	0.95
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.213
30% Bioavailability (F30%):	0.777

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.856
Plasma Protein Binding (PPB):	87.23550415039062%
Volume Distribution (VD):	2.438
Pgp-substrate:	10.449079513549805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.099
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.398
CYP2C19-substrate:	0.698
CYP2C9-inhibitor:	0.606
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.909
CYP3A4-substrate:	0.63

ADMET: Excretion

Clearance (CL):	9.715
Half-life (T1/2):	0.169

ADMET: Toxicity

hERG Blockers:	0.834
Human Hepatotoxicity (H-HT):	0.656
Drug-inuced Liver Injury (DILI):	0.164
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.083
Carcinogencity:	0.481
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC162812

Natural Product ID:	NPC162812
*Common Name:**	Decaturin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TWFKYYSBMIGIGV-SCBNGLQJSA-N
Standard InCHI:	InChI=1S/C30H35NO6/c1-17-7-8-22-27(4,10-9-21-26(2,3)29(34)12-11-28(21,22)16-35-29)30(17)24(32)23-20(37-30)14-19(36-25(23)33)18-6-5-13-31-15-18/h5-7,13-15,21-22,24,32,34H,8-12,16H2,1-4H3/t21-,22-,24-,27+,28+,29-,30+/m0/s1
SMILES:	CC1=CC[C@H]2[C@@](C)(CC[C@H]3C(C)(C)[C@@]4(CC[C@]23CO4)O)[C@@]21[C@H](c1c(cc(c3cccnc3)oc1=O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517512
PubChem CID:	10896433
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO302	Penicillium thiersii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787428]
NPO3117	Aconitum legendrei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15125.2	Taxus wallichiana var. wallichiana	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3117	Aconitum legendrei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3117	Aconitum legendrei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8763	Erythrina herbacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6764	Dianthus japonicus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16983	Persea obovatifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9566	Abies canadensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10069	Chaptalia nutans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15125.2	Taxus wallichiana var. wallichiana	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10990	Myristica surinamensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9135	Ligularia fauriei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3117	Aconitum legendrei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2803	Lyonetia clerkella	Species	Lyonetiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO302	Penicillium thiersii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11104	Diadema antillarum	Species	Diadematidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9915	Pieris brassicae	Species	Pieridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2010	Viburnum ichangense	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8958	Centella erecta	Species	Apiaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	89.0	%	PMID[529860]

☑ 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 NPC162812 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	445
0.1-0.2	1861
0.2-0.3	4411
0.3-0.4	10759
0.4-0.5	10396
0.5-0.6	12423
0.6-0.7	2122
0.7-0.8	207
0.8-0.85	66
0.85-0.9	3
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9742	High Similarity	NPC30570
0.9689	High Similarity	NPC292517
0.9531	High Similarity	NPC475835
0.8889	High Similarity	NPC477902
0.8804	High Similarity	NPC124029
0.8768	High Similarity	NPC477906
0.8738	High Similarity	NPC216428
0.8725	High Similarity	NPC264674
0.8714	High Similarity	NPC211920
0.8711	High Similarity	NPC103230
0.8696	High Similarity	NPC477901
0.8689	High Similarity	NPC62367
0.8683	High Similarity	NPC477909
0.8683	High Similarity	NPC477910
0.8683	High Similarity	NPC477907
0.8683	High Similarity	NPC42678
0.8663	High Similarity	NPC304179
0.8663	High Similarity	NPC472550
0.8663	High Similarity	NPC48042
0.8654	High Similarity	NPC477912
0.8627	High Similarity	NPC472553
0.8614	High Similarity	NPC63041
0.8612	High Similarity	NPC235364
0.8578	High Similarity	NPC148860
0.8565	High Similarity	NPC477903
0.8558	High Similarity	NPC472555
0.8551	High Similarity	NPC206343
0.8551	High Similarity	NPC477908
0.8531	High Similarity	NPC26881
0.8531	High Similarity	NPC477899
0.8531	High Similarity	NPC477900
0.8524	High Similarity	NPC477911
0.8483	Intermediate Similarity	NPC471980
0.8469	Intermediate Similarity	NPC84815
0.8469	Intermediate Similarity	NPC301368
0.8462	Intermediate Similarity	NPC471016
0.8462	Intermediate Similarity	NPC471014
0.8462	Intermediate Similarity	NPC475408
0.8454	Intermediate Similarity	NPC319128
0.8454	Intermediate Similarity	NPC228331
0.8436	Intermediate Similarity	NPC127026
0.8436	Intermediate Similarity	NPC127720
0.8421	Intermediate Similarity	NPC294579
0.8421	Intermediate Similarity	NPC144779
0.8419	Intermediate Similarity	NPC96801
0.8419	Intermediate Similarity	NPC150698
0.8413	Intermediate Similarity	NPC470306
0.8373	Intermediate Similarity	NPC6981
0.8372	Intermediate Similarity	NPC91125
0.8364	Intermediate Similarity	NPC475601
0.8295	Intermediate Similarity	NPC469748
0.8278	Intermediate Similarity	NPC4421
0.8271	Intermediate Similarity	NPC328154
0.8271	Intermediate Similarity	NPC475137
0.8271	Intermediate Similarity	NPC473850
0.8271	Intermediate Similarity	NPC475498
0.8246	Intermediate Similarity	NPC212768
0.8246	Intermediate Similarity	NPC473089
0.8246	Intermediate Similarity	NPC75600
0.8246	Intermediate Similarity	NPC6576
0.8246	Intermediate Similarity	NPC158020
0.8246	Intermediate Similarity	NPC473115
0.8241	Intermediate Similarity	NPC471977
0.8241	Intermediate Similarity	NPC471190
0.8241	Intermediate Similarity	NPC470486
0.8241	Intermediate Similarity	NPC475644
0.8224	Intermediate Similarity	NPC76565
0.8224	Intermediate Similarity	NPC250807
0.8224	Intermediate Similarity	NPC57797
0.8213	Intermediate Similarity	NPC472752
0.8211	Intermediate Similarity	NPC30456
0.8194	Intermediate Similarity	NPC475631
0.8194	Intermediate Similarity	NPC328186
0.8194	Intermediate Similarity	NPC122968
0.8194	Intermediate Similarity	NPC475600
0.8194	Intermediate Similarity	NPC476110
0.8194	Intermediate Similarity	NPC477787
0.8194	Intermediate Similarity	NPC228377
0.8194	Intermediate Similarity	NPC87152
0.8165	Intermediate Similarity	NPC475303
0.8165	Intermediate Similarity	NPC316841
0.8165	Intermediate Similarity	NPC475596
0.8157	Intermediate Similarity	NPC475362
0.8148	Intermediate Similarity	NPC473506
0.8136	Intermediate Similarity	NPC170751
0.8136	Intermediate Similarity	NPC35208
0.8136	Intermediate Similarity	NPC475426
0.8136	Intermediate Similarity	NPC327769
0.8111	Intermediate Similarity	NPC146824
0.8107	Intermediate Similarity	NPC289086
0.8095	Intermediate Similarity	NPC476467
0.8091	Intermediate Similarity	NPC237702
0.8091	Intermediate Similarity	NPC238278
0.8082	Intermediate Similarity	NPC473689
0.8082	Intermediate Similarity	NPC292416
0.8072	Intermediate Similarity	NPC253482
0.8054	Intermediate Similarity	NPC475406
0.8045	Intermediate Similarity	NPC244839
0.8045	Intermediate Similarity	NPC320324
0.8045	Intermediate Similarity	NPC319880
0.8044	Intermediate Similarity	NPC475648
0.8018	Intermediate Similarity	NPC38959
0.8018	Intermediate Similarity	NPC327904
0.8018	Intermediate Similarity	NPC233727
0.8009	Intermediate Similarity	NPC477788
0.7945	Intermediate Similarity	NPC285411
0.7945	Intermediate Similarity	NPC14116
0.793	Intermediate Similarity	NPC476090
0.7909	Intermediate Similarity	NPC311196
0.7909	Intermediate Similarity	NPC134384
0.7883	Intermediate Similarity	NPC213143
0.7851	Intermediate Similarity	NPC471013
0.7851	Intermediate Similarity	NPC180668
0.7851	Intermediate Similarity	NPC148896
0.784	Intermediate Similarity	NPC280473
0.784	Intermediate Similarity	NPC323551
0.7826	Intermediate Similarity	NPC470279
0.7814	Intermediate Similarity	NPC193361
0.7814	Intermediate Similarity	NPC62844
0.781	Intermediate Similarity	NPC309498
0.7804	Intermediate Similarity	NPC41724
0.7804	Intermediate Similarity	NPC51008
0.7778	Intermediate Similarity	NPC160127
0.7778	Intermediate Similarity	NPC50997
0.7768	Intermediate Similarity	NPC471015
0.7757	Intermediate Similarity	NPC111732
0.7742	Intermediate Similarity	NPC187494
0.7729	Intermediate Similarity	NPC324245
0.7729	Intermediate Similarity	NPC320748
0.7723	Intermediate Similarity	NPC325775
0.7723	Intermediate Similarity	NPC328798
0.7716	Intermediate Similarity	NPC476516
0.7716	Intermediate Similarity	NPC10904
0.7703	Intermediate Similarity	NPC328559
0.7703	Intermediate Similarity	NPC32451
0.7681	Intermediate Similarity	NPC329024
0.7662	Intermediate Similarity	NPC475533
0.7656	Intermediate Similarity	NPC79223
0.7639	Intermediate Similarity	NPC165837
0.7636	Intermediate Similarity	NPC253314
0.7629	Intermediate Similarity	NPC475315
0.7629	Intermediate Similarity	NPC324619
0.7628	Intermediate Similarity	NPC470189
0.7628	Intermediate Similarity	NPC40919
0.7615	Intermediate Similarity	NPC471978
0.7612	Intermediate Similarity	NPC327373
0.7606	Intermediate Similarity	NPC156044
0.7605	Intermediate Similarity	NPC473833
0.758	Intermediate Similarity	NPC319556
0.757	Intermediate Similarity	NPC470190
0.7566	Intermediate Similarity	NPC471004
0.756	Intermediate Similarity	NPC59033
0.756	Intermediate Similarity	NPC317672
0.7525	Intermediate Similarity	NPC325093
0.7525	Intermediate Similarity	NPC322043
0.7524	Intermediate Similarity	NPC127647
0.7512	Intermediate Similarity	NPC25442
0.7512	Intermediate Similarity	NPC12944
0.7511	Intermediate Similarity	NPC53255
0.7511	Intermediate Similarity	NPC475301
0.7511	Intermediate Similarity	NPC85879
0.7511	Intermediate Similarity	NPC326930
0.7489	Intermediate Similarity	NPC207531
0.7479	Intermediate Similarity	NPC13603
0.7469	Intermediate Similarity	NPC328928
0.7468	Intermediate Similarity	NPC476517
0.7452	Intermediate Similarity	NPC289786
0.7451	Intermediate Similarity	NPC318020
0.7449	Intermediate Similarity	NPC471979
0.7427	Intermediate Similarity	NPC182814
0.734	Intermediate Similarity	NPC471997
0.7301	Intermediate Similarity	NPC235885
0.7265	Intermediate Similarity	NPC314270
0.7265	Intermediate Similarity	NPC37473
0.7251	Intermediate Similarity	NPC20593
0.7244	Intermediate Similarity	NPC2395
0.7217	Intermediate Similarity	NPC473053
0.7209	Intermediate Similarity	NPC155792
0.7179	Intermediate Similarity	NPC473565
0.7175	Intermediate Similarity	NPC204491
0.7162	Intermediate Similarity	NPC317752
0.7162	Intermediate Similarity	NPC57690
0.7149	Intermediate Similarity	NPC141428
0.7149	Intermediate Similarity	NPC478045
0.7118	Intermediate Similarity	NPC472762
0.7117	Intermediate Similarity	NPC151976
0.7117	Intermediate Similarity	NPC318299
0.7116	Intermediate Similarity	NPC123395
0.7111	Intermediate Similarity	NPC82070
0.71	Intermediate Similarity	NPC477975
0.7095	Intermediate Similarity	NPC44354
0.7089	Intermediate Similarity	NPC146724
0.7071	Intermediate Similarity	NPC107123
0.7067	Intermediate Similarity	NPC207851
0.705	Intermediate Similarity	NPC474217
0.7045	Intermediate Similarity	NPC474905
0.7031	Intermediate Similarity	NPC475271
0.7025	Intermediate Similarity	NPC183537
0.7022	Intermediate Similarity	NPC476114
0.7022	Intermediate Similarity	NPC203614

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 NPC162812 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	605
0.2-0.3	946
0.3-0.4	2132
0.4-0.5	2810
0.5-0.6	1906
0.6-0.7	453
0.7-0.8	15
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
0.7817	Intermediate Similarity	NPD8468	Phase 2
0.7534	Intermediate Similarity	NPD8325	Phase 3
0.7534	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD8326	Phase 3
0.7463	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7396	Approved
0.7398	Intermediate Similarity	NPD6635	Approved
0.7352	Intermediate Similarity	NPD7069	Discontinued
0.7327	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5088	Discontinued
0.726	Intermediate Similarity	NPD7233	Approved
0.726	Intermediate Similarity	NPD7234	Approved
0.7215	Intermediate Similarity	NPD6529	Discontinued
0.7157	Intermediate Similarity	NPD6641	Approved
0.7157	Intermediate Similarity	NPD6642	Approved
0.7149	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8063	Discontinued
0.7143	Intermediate Similarity	NPD6026	Approved
0.7123	Intermediate Similarity	NPD6361	Phase 2
0.7097	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD8409	Suspended
0.7048	Intermediate Similarity	NPD8479	Phase 2
0.7018	Intermediate Similarity	NPD6298	Discontinued
0.7017	Intermediate Similarity	NPD1483	Discontinued
0.7009	Intermediate Similarity	NPD3794	Approved
0.7009	Intermediate Similarity	NPD4427	Phase 2
0.7009	Intermediate Similarity	NPD3795	Approved
0.7004	Intermediate Similarity	NPD7886	Phase 2
0.7004	Intermediate Similarity	NPD7885	Phase 2
0.7	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD53	Approved
0.6991	Remote Similarity	NPD7777	Approved
0.6991	Remote Similarity	NPD7778	Approved
0.695	Remote Similarity	NPD2511	Approved
0.6943	Remote Similarity	NPD5147	Discontinued
0.6923	Remote Similarity	NPD7010	Phase 3
0.6916	Remote Similarity	NPD4989	Phase 2
0.6914	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.688	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4086	Phase 1
0.6851	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.685	Remote Similarity	NPD820	Phase 3
0.6849	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4375	Approved
0.6829	Remote Similarity	NPD8370	Discontinued
0.682	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7562	Approved
0.681	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4038	Approved
0.6802	Remote Similarity	NPD32	Approved
0.6802	Remote Similarity	NPD4122	Approved
0.6802	Remote Similarity	NPD4034	Approved
0.6802	Remote Similarity	NPD4035	Approved
0.6802	Remote Similarity	NPD4037	Approved
0.6802	Remote Similarity	NPD4033	Approved
0.6802	Remote Similarity	NPD4036	Approved
0.6802	Remote Similarity	NPD31	Approved
0.6802	Remote Similarity	NPD4039	Approved
0.6792	Remote Similarity	NPD4889	Approved
0.6787	Remote Similarity	NPD7955	Approved
0.6787	Remote Similarity	NPD7956	Approved
0.6754	Remote Similarity	NPD7707	Approved
0.6754	Remote Similarity	NPD4897	Phase 2
0.6752	Remote Similarity	NPD7426	Phase 1
0.6751	Remote Similarity	NPD7797	Approved
0.6751	Remote Similarity	NPD7796	Approved
0.6749	Remote Similarity	NPD7967	Discontinued
0.6744	Remote Similarity	NPD3321	Discontinued
0.6736	Remote Similarity	NPD5891	Approved
0.6728	Remote Similarity	NPD4551	Phase 2
0.6728	Remote Similarity	NPD4526	Approved
0.6728	Remote Similarity	NPD4529	Approved
0.6728	Remote Similarity	NPD4528	Approved
0.6726	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD3394	Approved
0.6725	Remote Similarity	NPD3389	Approved
0.6725	Remote Similarity	NPD3393	Approved
0.6724	Remote Similarity	NPD5506	Approved
0.6724	Remote Similarity	NPD5507	Approved
0.6715	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6206	Phase 1
0.6711	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4021	Phase 2
0.6697	Remote Similarity	NPD4601	Approved
0.6697	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4600	Approved
0.6696	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7957	Phase 1
0.6694	Remote Similarity	NPD6276	Discontinued
0.6693	Remote Similarity	NPD7708	Approved
0.6684	Remote Similarity	NPD2896	Discontinued
0.6682	Remote Similarity	NPD4376	Phase 3
0.6681	Remote Similarity	NPD3280	Approved
0.6667	Remote Similarity	NPD3815	Phase 1
0.6667	Remote Similarity	NPD3816	Phase 1
0.6667	Remote Similarity	NPD6281	Approved
0.6667	Remote Similarity	NPD8412	Phase 1
0.6654	Remote Similarity	NPD7803	Approved
0.6651	Remote Similarity	NPD8021	Approved
0.6651	Remote Similarity	NPD8020	Approved
0.6651	Remote Similarity	NPD3386	Phase 2
0.6638	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD8485	Approved
0.6636	Remote Similarity	NPD5003	Discontinued
0.6636	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD2336	Approved
0.6635	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4417	Approved
0.662	Remote Similarity	NPD4334	Discontinued
0.661	Remote Similarity	NPD5640	Discontinued
0.661	Remote Similarity	NPD8289	Discontinued
0.6609	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3922	Approved
0.6606	Remote Similarity	NPD3923	Approved
0.6606	Remote Similarity	NPD3924	Approved
0.6606	Remote Similarity	NPD3921	Approved
0.6606	Remote Similarity	NPD6569	Phase 2
0.6606	Remote Similarity	NPD6665	Discontinued
0.6601	Remote Similarity	NPD2581	Approved
0.6601	Remote Similarity	NPD2582	Approved
0.6597	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7395	Discontinued
0.6595	Remote Similarity	NPD6568	Discontinued
0.659	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.659	Remote Similarity	NPD8361	Approved
0.659	Remote Similarity	NPD8360	Approved
0.6588	Remote Similarity	NPD1032	Phase 2
0.6584	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD2509	Approved
0.6564	Remote Similarity	NPD2510	Approved
0.6562	Remote Similarity	NPD7561	Approved
0.6556	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7470	Discontinued
0.6549	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD4501	Approved
0.6547	Remote Similarity	NPD4500	Approved
0.6547	Remote Similarity	NPD6479	Discontinued
0.654	Remote Similarity	NPD5100	Phase 3
0.6537	Remote Similarity	NPD5149	Phase 2
0.6537	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4437	Phase 3
0.6533	Remote Similarity	NPD5513	Phase 2
0.6533	Remote Similarity	NPD5487	Phase 1
0.6532	Remote Similarity	NPD6261	Phase 3
0.6524	Remote Similarity	NPD7878	Phase 2
0.652	Remote Similarity	NPD5429	Discontinued
0.6516	Remote Similarity	NPD2307	Discontinued
0.6515	Remote Similarity	NPD3813	Approved
0.6515	Remote Similarity	NPD6494	Phase 2
0.6515	Remote Similarity	NPD7558	Phase 2
0.6514	Remote Similarity	NPD2565	Phase 2
0.6514	Remote Similarity	NPD2564	Approved
0.6514	Remote Similarity	NPD8435	Approved
0.6514	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD4301	Approved
0.6506	Remote Similarity	NPD8101	Phase 3
0.6504	Remote Similarity	NPD2831	Approved
0.6502	Remote Similarity	NPD6874	Approved
0.6502	Remote Similarity	NPD6248	Phase 2
0.6502	Remote Similarity	NPD6249	Phase 2
0.65	Remote Similarity	NPD9271	Approved
0.6498	Remote Similarity	NPD6791	Phase 2
0.6498	Remote Similarity	NPD3925	Approved
0.6493	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.649	Remote Similarity	NPD7417	Discontinued
0.6489	Remote Similarity	NPD7187	Phase 2
0.6489	Remote Similarity	NPD8465	Approved
0.6489	Remote Similarity	NPD8466	Approved
0.6489	Remote Similarity	NPD8467	Approved
0.6488	Remote Similarity	NPD5255	Approved
0.6483	Remote Similarity	NPD8356	Approved
0.6482	Remote Similarity	NPD7169	Suspended
0.6476	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD5015	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD6219	Discontinued
0.6471	Remote Similarity	NPD3396	Approved
0.6471	Remote Similarity	NPD3395	Approved
0.646	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4315	Phase 2
0.6454	Remote Similarity	NPD7859	Phase 2
0.6453	Remote Similarity	NPD1926	Approved
0.6453	Remote Similarity	NPD3354	Phase 2
0.645	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5898	Approved
0.6449	Remote Similarity	NPD5899	Approved
0.6449	Remote Similarity	NPD5897	Approved
0.6448	Remote Similarity	NPD8364	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