NPASS Compound

Structure

NPC228477 OpenBabel07101718202D 32 36 0 0 1 0 0 0 0 0999 V2000 -3.2619 -2.1039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7615 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -1.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9781 -1.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2659 -0.3317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4594 0.8955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -1.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4844 1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4594 -0.9064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4844 -1.1290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4781 -1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8932 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -0.5055 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8366 1.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 0.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9706 0.4945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8932 -0.0055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9781 1.5241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9781 -0.2079 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 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 6 26 1 0 0 0 0 7 9 2 0 0 0 0 7 18 1 0 0 0 0 8 10 1 0 0 0 0 8 20 1 0 0 0 0 9 25 1 0 0 0 0 10 26 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 27 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 31 1 0 0 0 0 18 28 2 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 1 0 0 0 21 23 1 0 0 0 0 21 29 1 6 0 0 0 22 32 1 0 0 0 0 23 25 1 1 0 0 0 23 26 1 0 0 0 0 24 30 2 0 0 0 0 24 31 1 0 0 0 0 25 5 1 1 0 0 0 26 27 1 6 0 0 0 27 13 1 1 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.22
Volume:	458.262
LogP:	3.237
LogD:	3.001
LogS:	-4.383
# Rotatable Bonds:	0
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.611
Synthetic Accessibility Score:	5.397
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.885
MDCK Permeability:	2.4010258130147122e-05
Pgp-inhibitor:	0.441
Pgp-substrate:	0.924
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.443

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.455
Plasma Protein Binding (PPB):	92.26671600341797%
Volume Distribution (VD):	2.468
Pgp-substrate:	5.55809211730957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.792
CYP2C19-inhibitor:	0.248
CYP2C19-substrate:	0.83
CYP2C9-inhibitor:	0.714
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.562
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.926
CYP3A4-substrate:	0.781

ADMET: Excretion

Clearance (CL):	5.826
Half-life (T1/2):	0.435

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.493
Drug-inuced Liver Injury (DILI):	0.143
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.492
Maximum Recommended Daily Dose:	0.864
Skin Sensitization:	0.268
Carcinogencity:	0.583
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC228477

Natural Product ID:	NPC228477
*Common Name:**	Brevione G
IUPAC Name:	(1'R,2S,4'aR,6'aS,11'aS,11'bR)-1'-hydroxy-3',4'a,6,7,7',11'a-hexamethylspiro[3H-furo[3,2-c]pyran-2,4'-5,6,6a,11b-tetrahydro-1H-cyclohepta[a]naphthalene]-4,9'-dione
Synonyms:	Brevione G
Standard InCHIKey:	JTYNVLZPECDEQA-KHLKASDESA-N
Standard InCHI:	InChI=1S/C27H32O5/c1-14-11-18(28)7-9-25(5)20(14)8-10-26(6)23(25)21(29)12-15(2)27(26)13-19-22(32-27)16(3)17(4)31-24(19)30/h7,9,11-12,20-21,23,29H,8,10,13H2,1-6H3/t20-,21+,23+,25-,26+,27-/m0/s1
SMILES:	CC1=CC(=O)C=C[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2[C@@H](C=C(C)[C@]21Cc1c(c(C)c(C)oc1=O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL550770
PubChem CID:	44139897
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives

*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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]

☑ 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
EC50	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	GI	=	44.9	%	PMID[518040]
NPT6228	Organism	HIV-1 M:B_Lai	HIV-1 M:B_Lai	EC50	>	50000.0	nM	PMID[518040]

☑ 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 NPC228477 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	329
0.1-0.2	1284
0.2-0.3	2690
0.3-0.4	6006
0.4-0.5	11605
0.5-0.6	8386
0.6-0.7	7763
0.7-0.8	4502
0.8-0.85	124
0.85-0.9	4
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC137911
0.8627	High Similarity	NPC208094
0.8585	High Similarity	NPC266570
0.8447	Intermediate Similarity	NPC202705
0.8447	Intermediate Similarity	NPC53844
0.8431	Intermediate Similarity	NPC295347
0.8426	Intermediate Similarity	NPC220155
0.8411	Intermediate Similarity	NPC34768
0.8411	Intermediate Similarity	NPC478052
0.8381	Intermediate Similarity	NPC244456
0.8381	Intermediate Similarity	NPC469657
0.8365	Intermediate Similarity	NPC316598
0.8364	Intermediate Similarity	NPC474315
0.8333	Intermediate Similarity	NPC91034
0.8333	Intermediate Similarity	NPC477130
0.8333	Intermediate Similarity	NPC477129
0.8318	Intermediate Similarity	NPC118911
0.8302	Intermediate Similarity	NPC469606
0.8302	Intermediate Similarity	NPC273005
0.8302	Intermediate Similarity	NPC31058
0.83	Intermediate Similarity	NPC5509
0.8288	Intermediate Similarity	NPC236217
0.8286	Intermediate Similarity	NPC476299
0.8286	Intermediate Similarity	NPC54705
0.8286	Intermediate Similarity	NPC474012
0.8276	Intermediate Similarity	NPC287236
0.8273	Intermediate Similarity	NPC37116
0.8252	Intermediate Similarity	NPC209355
0.8241	Intermediate Similarity	NPC477125
0.8241	Intermediate Similarity	NPC469607
0.8241	Intermediate Similarity	NPC189863
0.823	Intermediate Similarity	NPC64318
0.8218	Intermediate Similarity	NPC220454
0.8218	Intermediate Similarity	NPC212679
0.8218	Intermediate Similarity	NPC469595
0.8214	Intermediate Similarity	NPC122056
0.8214	Intermediate Similarity	NPC469463
0.8214	Intermediate Similarity	NPC469454
0.8214	Intermediate Similarity	NPC469496
0.8214	Intermediate Similarity	NPC25909
0.8208	Intermediate Similarity	NPC168319
0.8208	Intermediate Similarity	NPC115862
0.8208	Intermediate Similarity	NPC194028
0.8208	Intermediate Similarity	NPC472637
0.819	Intermediate Similarity	NPC478056
0.819	Intermediate Similarity	NPC108368
0.819	Intermediate Similarity	NPC57079
0.8173	Intermediate Similarity	NPC16967
0.8165	Intermediate Similarity	NPC179380
0.8155	Intermediate Similarity	NPC476415
0.8142	Intermediate Similarity	NPC67259
0.8142	Intermediate Similarity	NPC147912
0.8131	Intermediate Similarity	NPC235369
0.8131	Intermediate Similarity	NPC32577
0.8131	Intermediate Similarity	NPC114540
0.8131	Intermediate Similarity	NPC155332
0.8131	Intermediate Similarity	NPC476081
0.8131	Intermediate Similarity	NPC136289
0.8119	Intermediate Similarity	NPC284561
0.8113	Intermediate Similarity	NPC477720
0.8113	Intermediate Similarity	NPC227865
0.8113	Intermediate Similarity	NPC266955
0.8108	Intermediate Similarity	NPC16270
0.8108	Intermediate Similarity	NPC29133
0.81	Intermediate Similarity	NPC312561
0.8095	Intermediate Similarity	NPC132753
0.8095	Intermediate Similarity	NPC175351
0.8095	Intermediate Similarity	NPC151681
0.8095	Intermediate Similarity	NPC121402
0.8095	Intermediate Similarity	NPC38530
0.8095	Intermediate Similarity	NPC84335
0.8095	Intermediate Similarity	NPC253826
0.8095	Intermediate Similarity	NPC224356
0.8087	Intermediate Similarity	NPC709
0.8087	Intermediate Similarity	NPC186525
0.8087	Intermediate Similarity	NPC50774
0.8077	Intermediate Similarity	NPC183012
0.8077	Intermediate Similarity	NPC171395
0.8073	Intermediate Similarity	NPC478208
0.8058	Intermediate Similarity	NPC476416
0.8058	Intermediate Similarity	NPC115021
0.8056	Intermediate Similarity	NPC183570
0.8039	Intermediate Similarity	NPC469372
0.8039	Intermediate Similarity	NPC232426
0.8039	Intermediate Similarity	NPC281942
0.8037	Intermediate Similarity	NPC99411
0.8037	Intermediate Similarity	NPC81530
0.8037	Intermediate Similarity	NPC476240
0.8037	Intermediate Similarity	NPC476223
0.8037	Intermediate Similarity	NPC115899
0.8037	Intermediate Similarity	NPC224720
0.8036	Intermediate Similarity	NPC304180
0.8036	Intermediate Similarity	NPC255401
0.8036	Intermediate Similarity	NPC324683
0.8036	Intermediate Similarity	NPC179798
0.8036	Intermediate Similarity	NPC470961
0.8036	Intermediate Similarity	NPC284162
0.802	Intermediate Similarity	NPC472302
0.802	Intermediate Similarity	NPC24816
0.8019	Intermediate Similarity	NPC235464
0.8019	Intermediate Similarity	NPC166745
0.8019	Intermediate Similarity	NPC471717
0.8019	Intermediate Similarity	NPC98868
0.8017	Intermediate Similarity	NPC156745
0.8017	Intermediate Similarity	NPC236918
0.8	Intermediate Similarity	NPC472363
0.8	Intermediate Similarity	NPC286528
0.8	Intermediate Similarity	NPC470493
0.8	Intermediate Similarity	NPC472362
0.8	Intermediate Similarity	NPC67321
0.8	Intermediate Similarity	NPC140055
0.8	Intermediate Similarity	NPC302788
0.8	Intermediate Similarity	NPC470492
0.8	Intermediate Similarity	NPC250757
0.8	Intermediate Similarity	NPC20302
0.8	Intermediate Similarity	NPC475294
0.8	Intermediate Similarity	NPC183580
0.8	Intermediate Similarity	NPC154526
0.8	Intermediate Similarity	NPC187435
0.8	Intermediate Similarity	NPC312824
0.8	Intermediate Similarity	NPC167606
0.8	Intermediate Similarity	NPC301534
0.7982	Intermediate Similarity	NPC472868
0.7982	Intermediate Similarity	NPC272632
0.7982	Intermediate Similarity	NPC474181
0.7981	Intermediate Similarity	NPC38830
0.7981	Intermediate Similarity	NPC191521
0.7965	Intermediate Similarity	NPC221144
0.7965	Intermediate Similarity	NPC191620
0.7963	Intermediate Similarity	NPC475320
0.7961	Intermediate Similarity	NPC233345
0.7961	Intermediate Similarity	NPC303697
0.7961	Intermediate Similarity	NPC186363
0.7961	Intermediate Similarity	NPC252433
0.7961	Intermediate Similarity	NPC141831
0.7949	Intermediate Similarity	NPC329080
0.7949	Intermediate Similarity	NPC472759
0.7949	Intermediate Similarity	NPC19336
0.7949	Intermediate Similarity	NPC185876
0.7949	Intermediate Similarity	NPC475885
0.7949	Intermediate Similarity	NPC474370
0.7946	Intermediate Similarity	NPC473627
0.7946	Intermediate Similarity	NPC478211
0.7946	Intermediate Similarity	NPC5103
0.7944	Intermediate Similarity	NPC476274
0.7944	Intermediate Similarity	NPC290802
0.7941	Intermediate Similarity	NPC118011
0.7941	Intermediate Similarity	NPC36668
0.7941	Intermediate Similarity	NPC210216
0.7941	Intermediate Similarity	NPC168131
0.7941	Intermediate Similarity	NPC174342
0.7931	Intermediate Similarity	NPC472760
0.7931	Intermediate Similarity	NPC475913
0.7931	Intermediate Similarity	NPC146786
0.7928	Intermediate Similarity	NPC275539
0.7928	Intermediate Similarity	NPC189075
0.7925	Intermediate Similarity	NPC107243
0.7925	Intermediate Similarity	NPC254496
0.7925	Intermediate Similarity	NPC474343
0.7925	Intermediate Similarity	NPC170131
0.7913	Intermediate Similarity	NPC176840
0.7909	Intermediate Similarity	NPC81630
0.79	Intermediate Similarity	NPC189311
0.7895	Intermediate Similarity	NPC73050
0.7895	Intermediate Similarity	NPC321496
0.7895	Intermediate Similarity	NPC56448
0.789	Intermediate Similarity	NPC471208
0.789	Intermediate Similarity	NPC473283
0.789	Intermediate Similarity	NPC72151
0.789	Intermediate Similarity	NPC236390
0.789	Intermediate Similarity	NPC280566
0.789	Intermediate Similarity	NPC475526
0.789	Intermediate Similarity	NPC120321
0.789	Intermediate Similarity	NPC329345
0.789	Intermediate Similarity	NPC478057
0.789	Intermediate Similarity	NPC112009
0.7885	Intermediate Similarity	NPC205034
0.7885	Intermediate Similarity	NPC162615
0.7885	Intermediate Similarity	NPC152778
0.7885	Intermediate Similarity	NPC139692
0.7885	Intermediate Similarity	NPC242069
0.7885	Intermediate Similarity	NPC469939
0.7881	Intermediate Similarity	NPC67569
0.7876	Intermediate Similarity	NPC97939
0.7876	Intermediate Similarity	NPC262083
0.7876	Intermediate Similarity	NPC247031
0.7876	Intermediate Similarity	NPC100329
0.7876	Intermediate Similarity	NPC132790
0.7876	Intermediate Similarity	NPC471484
0.787	Intermediate Similarity	NPC471412
0.787	Intermediate Similarity	NPC303559
0.787	Intermediate Similarity	NPC282524
0.787	Intermediate Similarity	NPC63249
0.7864	Intermediate Similarity	NPC221111
0.7864	Intermediate Similarity	NPC145666
0.7864	Intermediate Similarity	NPC280149
0.7864	Intermediate Similarity	NPC182136
0.7864	Intermediate Similarity	NPC310479
0.7864	Intermediate Similarity	NPC51486
0.7863	Intermediate Similarity	NPC475834

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 NPC228477 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	897
0.2-0.3	1679
0.3-0.4	2547
0.4-0.5	2202
0.5-0.6	1101
0.6-0.7	351
0.7-0.8	84
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD7115	Discovery
0.7549	Intermediate Similarity	NPD1694	Approved
0.7547	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD6053	Discontinued
0.7456	Intermediate Similarity	NPD6899	Approved
0.7456	Intermediate Similarity	NPD6881	Approved
0.7455	Intermediate Similarity	NPD7639	Approved
0.7455	Intermediate Similarity	NPD7640	Approved
0.7453	Intermediate Similarity	NPD5281	Approved
0.7453	Intermediate Similarity	NPD5284	Approved
0.7431	Intermediate Similarity	NPD7902	Approved
0.7426	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6650	Approved
0.7414	Intermediate Similarity	NPD6649	Approved
0.7368	Intermediate Similarity	NPD5697	Approved
0.7364	Intermediate Similarity	NPD7638	Approved
0.7364	Intermediate Similarity	NPD4225	Approved
0.7358	Intermediate Similarity	NPD5785	Approved
0.7328	Intermediate Similarity	NPD7102	Approved
0.7328	Intermediate Similarity	NPD7290	Approved
0.7328	Intermediate Similarity	NPD6883	Approved
0.7315	Intermediate Similarity	NPD7748	Approved
0.7304	Intermediate Similarity	NPD6686	Approved
0.7304	Intermediate Similarity	NPD6011	Approved
0.729	Intermediate Similarity	NPD7515	Phase 2
0.7281	Intermediate Similarity	NPD5739	Approved
0.7281	Intermediate Similarity	NPD6675	Approved
0.7281	Intermediate Similarity	NPD6402	Approved
0.7281	Intermediate Similarity	NPD7128	Approved
0.7273	Intermediate Similarity	NPD6084	Phase 2
0.7273	Intermediate Similarity	NPD6083	Phase 2
0.7265	Intermediate Similarity	NPD8130	Phase 1
0.7265	Intermediate Similarity	NPD6869	Approved
0.7265	Intermediate Similarity	NPD6847	Approved
0.7265	Intermediate Similarity	NPD6617	Approved
0.7248	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6014	Approved
0.7241	Intermediate Similarity	NPD6372	Approved
0.7241	Intermediate Similarity	NPD6373	Approved
0.7241	Intermediate Similarity	NPD6013	Approved
0.7241	Intermediate Similarity	NPD6012	Approved
0.7203	Intermediate Similarity	NPD6882	Approved
0.7203	Intermediate Similarity	NPD8297	Approved
0.7179	Intermediate Similarity	NPD6371	Approved
0.7168	Intermediate Similarity	NPD5211	Phase 2
0.7156	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7900	Approved
0.7155	Intermediate Similarity	NPD7320	Approved
0.7154	Intermediate Similarity	NPD7503	Approved
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.713	Intermediate Similarity	NPD6411	Approved
0.713	Intermediate Similarity	NPD6079	Approved
0.7103	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5695	Phase 3
0.7069	Intermediate Similarity	NPD5701	Approved
0.7064	Intermediate Similarity	NPD5779	Approved
0.7064	Intermediate Similarity	NPD5778	Approved
0.7054	Intermediate Similarity	NPD7260	Phase 2
0.7054	Intermediate Similarity	NPD5696	Approved
0.7043	Intermediate Similarity	NPD5141	Approved
0.7037	Intermediate Similarity	NPD5207	Approved
0.7034	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6672	Approved
0.7009	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5737	Approved
0.7009	Intermediate Similarity	NPD6903	Approved
0.6991	Remote Similarity	NPD4696	Approved
0.6991	Remote Similarity	NPD5285	Approved
0.6991	Remote Similarity	NPD5286	Approved
0.6981	Remote Similarity	NPD5279	Phase 3
0.6981	Remote Similarity	NPD4623	Approved
0.6981	Remote Similarity	NPD4519	Discontinued
0.6975	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5693	Phase 1
0.6972	Remote Similarity	NPD6050	Approved
0.6972	Remote Similarity	NPD5694	Approved
0.6952	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD3665	Phase 1
0.6952	Remote Similarity	NPD3666	Approved
0.6952	Remote Similarity	NPD3133	Approved
0.6952	Remote Similarity	NPD4786	Approved
0.6944	Remote Similarity	NPD6101	Approved
0.6944	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5328	Approved
0.6937	Remote Similarity	NPD4629	Approved
0.6937	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5210	Approved
0.693	Remote Similarity	NPD5223	Approved
0.6923	Remote Similarity	NPD3667	Approved
0.6916	Remote Similarity	NPD3573	Approved
0.6911	Remote Similarity	NPD6335	Approved
0.6909	Remote Similarity	NPD4202	Approved
0.6903	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4695	Discontinued
0.6887	Remote Similarity	NPD5363	Approved
0.6881	Remote Similarity	NPD5692	Phase 3
0.6875	Remote Similarity	NPD5222	Approved
0.6875	Remote Similarity	NPD5221	Approved
0.6875	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5225	Approved
0.687	Remote Similarity	NPD4633	Approved
0.687	Remote Similarity	NPD5226	Approved
0.687	Remote Similarity	NPD5224	Approved
0.687	Remote Similarity	NPD7632	Discontinued
0.686	Remote Similarity	NPD4632	Approved
0.6857	Remote Similarity	NPD7154	Phase 3
0.6855	Remote Similarity	NPD7101	Approved
0.6855	Remote Similarity	NPD7100	Approved
0.6838	Remote Similarity	NPD6008	Approved
0.6829	Remote Similarity	NPD6317	Approved
0.6822	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7637	Suspended
0.6814	Remote Similarity	NPD4755	Approved
0.6814	Remote Similarity	NPD5173	Approved
0.681	Remote Similarity	NPD5174	Approved
0.681	Remote Similarity	NPD5175	Approved
0.6789	Remote Similarity	NPD6673	Approved
0.6789	Remote Similarity	NPD4753	Phase 2
0.6789	Remote Similarity	NPD6080	Approved
0.6789	Remote Similarity	NPD6904	Approved
0.678	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6313	Approved
0.6774	Remote Similarity	NPD6314	Approved
0.6748	Remote Similarity	NPD6274	Approved
0.6748	Remote Similarity	NPD6868	Approved
0.6746	Remote Similarity	NPD8513	Phase 3
0.6746	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD8039	Approved
0.6726	Remote Similarity	NPD4697	Phase 3
0.6699	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5282	Discontinued
0.6696	Remote Similarity	NPD6648	Approved
0.6696	Remote Similarity	NPD4700	Approved
0.6696	Remote Similarity	NPD6404	Discontinued
0.6694	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.6641	Remote Similarity	NPD7604	Phase 2
0.6639	Remote Similarity	NPD6412	Phase 2
0.6638	Remote Similarity	NPD5344	Discontinued
0.6636	Remote Similarity	NPD6051	Approved
0.6617	Remote Similarity	NPD6845	Suspended
0.6614	Remote Similarity	NPD8517	Approved
0.6614	Remote Similarity	NPD8515	Approved
0.6614	Remote Similarity	NPD8516	Approved
0.6614	Remote Similarity	NPD5983	Phase 2
0.6604	Remote Similarity	NPD4223	Phase 3
0.6604	Remote Similarity	NPD4270	Approved
0.6604	Remote Similarity	NPD5209	Approved
0.6604	Remote Similarity	NPD4269	Approved
0.6604	Remote Similarity	NPD4221	Approved
0.6602	Remote Similarity	NPD4756	Discovery
0.6589	Remote Similarity	NPD7492	Approved
0.6583	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4729	Approved
0.6583	Remote Similarity	NPD4730	Approved
0.6577	Remote Similarity	NPD46	Approved
0.6577	Remote Similarity	NPD6698	Approved
0.6577	Remote Similarity	NPD7838	Discovery
0.6574	Remote Similarity	NPD5329	Approved
0.6574	Remote Similarity	NPD1696	Phase 3
0.6557	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6001	Approved
0.6545	Remote Similarity	NPD5208	Approved
0.6542	Remote Similarity	NPD4788	Approved
0.6542	Remote Similarity	NPD5362	Discontinued
0.6538	Remote Similarity	NPD6336	Discontinued
0.6538	Remote Similarity	NPD6616	Approved
0.6535	Remote Similarity	NPD6054	Approved
0.6525	Remote Similarity	NPD4754	Approved
0.6515	Remote Similarity	NPD7319	Approved
0.6514	Remote Similarity	NPD5786	Approved
0.6514	Remote Similarity	NPD6098	Approved
0.6509	Remote Similarity	NPD5369	Approved
0.65	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5654	Approved
0.6489	Remote Similarity	NPD7078	Approved
0.6484	Remote Similarity	NPD6908	Approved
0.6484	Remote Similarity	NPD6909	Approved
0.6481	Remote Similarity	NPD4197	Approved
0.6481	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD3668	Phase 3
0.6475	Remote Similarity	NPD5250	Approved
0.6475	Remote Similarity	NPD5248	Approved
0.6475	Remote Similarity	NPD5251	Approved
0.6475	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD4634	Approved
0.6475	Remote Similarity	NPD5249	Phase 3

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