NPASS Compound

Structure

CID132054 OpenBabel06191715492D 23 25 0 0 1 0 0 0 0 0999 V2000 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 5.0064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0511 4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 4.4712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 3.3122 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 2 11 1 0 0 0 0 3 21 1 0 0 0 0 4 5 1 0 0 0 0 4 6 2 0 0 0 0 5 10 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 7 19 2 0 0 0 0 8 12 1 0 0 0 0 8 22 1 0 0 0 0 9 12 2 0 0 0 0 9 23 1 0 0 0 0 10 1 1 1 0 0 0 10 15 1 0 0 0 0 11 20 2 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 17 2 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 16 18 2 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.12
Volume:	319.711
LogP:	3.739
LogD:	3.157
LogS:	-4.442
# Rotatable Bonds:	5
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.633
Synthetic Accessibility Score:	3.82
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.754
MDCK Permeability:	2.0671750462497585e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.848
Plasma Protein Binding (PPB):	91.63129425048828%
Volume Distribution (VD):	1.96
Pgp-substrate:	10.13646125793457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.913
CYP1A2-substrate:	0.664
CYP2C19-inhibitor:	0.546
CYP2C19-substrate:	0.257
CYP2C9-inhibitor:	0.442
CYP2C9-substrate:	0.54
CYP2D6-inhibitor:	0.171
CYP2D6-substrate:	0.385
CYP3A4-inhibitor:	0.595
CYP3A4-substrate:	0.183

ADMET: Excretion

Clearance (CL):	6.194
Half-life (T1/2):	0.596

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.339
Drug-inuced Liver Injury (DILI):	0.515
AMES Toxicity:	0.954
Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.682
Carcinogencity:	0.957
Eye Corrosion:	0.2
Eye Irritation:	0.534
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC132054

Natural Product ID:	NPC132054
*Common Name:**	13-Acetoxy-14-Oxocacalohastin
IUPAC Name:	[(5S)-4-formyl-9-methoxy-5-methyl-5,6-dihydrobenzo[f][1]benzofuran-3-yl]methyl acetate
Synonyms:
Standard InCHIKey:	URGRYLWWOSDITP-JTQLQIEISA-N
Standard InCHI:	InChI=1S/C18H18O5/c1-10-5-4-6-13-15(10)14(7-19)16-12(8-22-11(2)20)9-23-18(16)17(13)21-3/h4,6-7,9-10H,5,8H2,1-3H3/t10-/m0/s1
SMILES:	O=Cc1c2[C@@H](C)CC=Cc2c(c2c1c(COC(=O)C)co2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463710
PubChem CID:	44566461
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

*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
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346940]
NPO12724	Roldana angulifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190472]
NPO16980	Callistemon lanceolatus	Species	Myrtaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18618463]
NPO16980	Callistemon lanceolatus	Species	Myrtaceae	Eukaryota	n.a.	flower	n.a.	PMID[18618463]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26722868]
NPO17352	Streptomyces mutabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27107984]
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[8588862]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11820	Amomum villosum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11820	Amomum villosum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29168	Jacobaea abrotanifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11820	Amomum villosum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15290.1	Petasites frigidus var. palmatus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29168	Jacobaea abrotanifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16980	Callistemon lanceolatus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12724	Roldana angulifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17352	Streptomyces mutabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18531	Streptomyces propurpuratus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11820	Amomum villosum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17113	Pertusaria sulphurata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12869	Quercus gambelii	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17896	Perymenium discolor	Species	Asteraceae	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
IC50	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT380	Cell Line	U-251	Homo sapiens	IC50	>	10000.0	nM	PMID[500904]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[500904]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[500904]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	>	10000.0	nM	PMID[500904]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[500904]
NPT311	Cell Line	SK-LU-1	Homo sapiens	IC50	>	10000.0	nM	PMID[500904]

☑ 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 NPC132054 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	443
0.1-0.2	1720
0.2-0.3	4088
0.3-0.4	9341
0.4-0.5	9343
0.5-0.6	4282
0.6-0.7	6625
0.7-0.8	6519
0.8-0.85	308
0.85-0.9	20
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9872	High Similarity	NPC298071
0.9497	High Similarity	NPC191012
0.9313	High Similarity	NPC279768
0.8788	High Similarity	NPC67450
0.8788	High Similarity	NPC155264
0.8788	High Similarity	NPC210460
0.8788	High Similarity	NPC193881
0.8773	High Similarity	NPC216092
0.8712	High Similarity	NPC243509
0.8675	High Similarity	NPC472895
0.8667	High Similarity	NPC179464
0.865	High Similarity	NPC33320
0.865	High Similarity	NPC250076
0.8606	High Similarity	NPC234536
0.8606	High Similarity	NPC78612
0.8598	High Similarity	NPC47623
0.8545	High Similarity	NPC264293
0.8521	High Similarity	NPC144288
0.8503	High Similarity	NPC173149
0.8503	High Similarity	NPC179015
0.8497	Intermediate Similarity	NPC475996
0.8494	Intermediate Similarity	NPC144843
0.8485	Intermediate Similarity	NPC139876
0.8434	Intermediate Similarity	NPC109238
0.843	Intermediate Similarity	NPC107244
0.8424	Intermediate Similarity	NPC15764
0.8412	Intermediate Similarity	NPC51404
0.8408	Intermediate Similarity	NPC27220
0.8402	Intermediate Similarity	NPC45760
0.8402	Intermediate Similarity	NPC186392
0.8395	Intermediate Similarity	NPC115869
0.8395	Intermediate Similarity	NPC474414
0.8372	Intermediate Similarity	NPC53917
0.8372	Intermediate Similarity	NPC224165
0.8344	Intermediate Similarity	NPC10429
0.8344	Intermediate Similarity	NPC60211
0.8333	Intermediate Similarity	NPC65846
0.8323	Intermediate Similarity	NPC309335
0.8323	Intermediate Similarity	NPC296540
0.8323	Intermediate Similarity	NPC24761
0.8314	Intermediate Similarity	NPC233956
0.8314	Intermediate Similarity	NPC62640
0.8314	Intermediate Similarity	NPC277510
0.8313	Intermediate Similarity	NPC471346
0.8304	Intermediate Similarity	NPC190351
0.8304	Intermediate Similarity	NPC20543
0.8304	Intermediate Similarity	NPC239440
0.8303	Intermediate Similarity	NPC261484
0.8294	Intermediate Similarity	NPC95715
0.8282	Intermediate Similarity	NPC98028
0.8282	Intermediate Similarity	NPC473732
0.8274	Intermediate Similarity	NPC19948
0.8274	Intermediate Similarity	NPC108767
0.8263	Intermediate Similarity	NPC65784
0.8263	Intermediate Similarity	NPC78944
0.8263	Intermediate Similarity	NPC21046
0.825	Intermediate Similarity	NPC62799
0.8246	Intermediate Similarity	NPC473095
0.8246	Intermediate Similarity	NPC473096
0.8242	Intermediate Similarity	NPC471456
0.8242	Intermediate Similarity	NPC3273
0.8239	Intermediate Similarity	NPC228209
0.8239	Intermediate Similarity	NPC8927
0.8232	Intermediate Similarity	NPC24232
0.8232	Intermediate Similarity	NPC475116
0.8229	Intermediate Similarity	NPC104682
0.8225	Intermediate Similarity	NPC308156
0.8221	Intermediate Similarity	NPC31132
0.8221	Intermediate Similarity	NPC191104
0.8218	Intermediate Similarity	NPC295914
0.8212	Intermediate Similarity	NPC295436
0.8208	Intermediate Similarity	NPC181523
0.8208	Intermediate Similarity	NPC65885
0.8208	Intermediate Similarity	NPC30550
0.8204	Intermediate Similarity	NPC228501
0.8204	Intermediate Similarity	NPC472299
0.8202	Intermediate Similarity	NPC240808
0.8198	Intermediate Similarity	NPC1827
0.8198	Intermediate Similarity	NPC246716
0.8198	Intermediate Similarity	NPC131866
0.8198	Intermediate Similarity	NPC28042
0.8198	Intermediate Similarity	NPC281835
0.8193	Intermediate Similarity	NPC115123
0.8193	Intermediate Similarity	NPC239113
0.8187	Intermediate Similarity	NPC272485
0.8187	Intermediate Similarity	NPC473094
0.8187	Intermediate Similarity	NPC302392
0.8187	Intermediate Similarity	NPC292788
0.8182	Intermediate Similarity	NPC75310
0.8182	Intermediate Similarity	NPC473664
0.8176	Intermediate Similarity	NPC473753
0.8176	Intermediate Similarity	NPC473766
0.8171	Intermediate Similarity	NPC475777
0.8171	Intermediate Similarity	NPC77179
0.8171	Intermediate Similarity	NPC246877
0.8171	Intermediate Similarity	NPC23553
0.8171	Intermediate Similarity	NPC221820
0.8167	Intermediate Similarity	NPC60848
0.8161	Intermediate Similarity	NPC66804
0.8161	Intermediate Similarity	NPC289147
0.8161	Intermediate Similarity	NPC139350
0.8161	Intermediate Similarity	NPC289244
0.816	Intermediate Similarity	NPC300983
0.816	Intermediate Similarity	NPC472298
0.816	Intermediate Similarity	NPC88445
0.8155	Intermediate Similarity	NPC472782
0.8155	Intermediate Similarity	NPC472962
0.8155	Intermediate Similarity	NPC472781
0.8155	Intermediate Similarity	NPC472961
0.8153	Intermediate Similarity	NPC233780
0.815	Intermediate Similarity	NPC475964
0.815	Intermediate Similarity	NPC247964
0.8148	Intermediate Similarity	NPC117463
0.8144	Intermediate Similarity	NPC143328
0.8144	Intermediate Similarity	NPC82733
0.8144	Intermediate Similarity	NPC76458
0.814	Intermediate Similarity	NPC41853
0.814	Intermediate Similarity	NPC26568
0.8136	Intermediate Similarity	NPC246153
0.8133	Intermediate Similarity	NPC268008
0.8133	Intermediate Similarity	NPC471746
0.8133	Intermediate Similarity	NPC80489
0.8129	Intermediate Similarity	NPC255787
0.8129	Intermediate Similarity	NPC291742
0.8121	Intermediate Similarity	NPC477962
0.8121	Intermediate Similarity	NPC180388
0.8121	Intermediate Similarity	NPC477961
0.8121	Intermediate Similarity	NPC477960
0.8118	Intermediate Similarity	NPC272750
0.8118	Intermediate Similarity	NPC173729
0.8118	Intermediate Similarity	NPC223006
0.8118	Intermediate Similarity	NPC15819
0.8118	Intermediate Similarity	NPC134047
0.8114	Intermediate Similarity	NPC8127
0.8114	Intermediate Similarity	NPC49667
0.811	Intermediate Similarity	NPC472406
0.811	Intermediate Similarity	NPC144010
0.8107	Intermediate Similarity	NPC269117
0.8107	Intermediate Similarity	NPC117985
0.8107	Intermediate Similarity	NPC99968
0.8107	Intermediate Similarity	NPC472783
0.8107	Intermediate Similarity	NPC472780
0.8107	Intermediate Similarity	NPC15212
0.8103	Intermediate Similarity	NPC72455
0.8103	Intermediate Similarity	NPC474568
0.8101	Intermediate Similarity	NPC174486
0.8098	Intermediate Similarity	NPC95526
0.8095	Intermediate Similarity	NPC333139
0.8095	Intermediate Similarity	NPC125713
0.8095	Intermediate Similarity	NPC68619
0.8092	Intermediate Similarity	NPC476641
0.8092	Intermediate Similarity	NPC10576
0.8092	Intermediate Similarity	NPC17219
0.809	Intermediate Similarity	NPC472662
0.809	Intermediate Similarity	NPC472663
0.8086	Intermediate Similarity	NPC473927
0.8086	Intermediate Similarity	NPC169682
0.8081	Intermediate Similarity	NPC42230
0.8081	Intermediate Similarity	NPC474948
0.8081	Intermediate Similarity	NPC234331
0.8081	Intermediate Similarity	NPC472660
0.8081	Intermediate Similarity	NPC167479
0.8075	Intermediate Similarity	NPC27106
0.8072	Intermediate Similarity	NPC41719
0.8072	Intermediate Similarity	NPC290927
0.807	Intermediate Similarity	NPC25361
0.807	Intermediate Similarity	NPC41689
0.807	Intermediate Similarity	NPC187923
0.8068	Intermediate Similarity	NPC5671
0.8061	Intermediate Similarity	NPC474388
0.8061	Intermediate Similarity	NPC118332
0.8061	Intermediate Similarity	NPC75377
0.8061	Intermediate Similarity	NPC472535
0.8061	Intermediate Similarity	NPC189773
0.8061	Intermediate Similarity	NPC474170
0.8059	Intermediate Similarity	NPC61141
0.8059	Intermediate Similarity	NPC272722
0.8059	Intermediate Similarity	NPC144557
0.8059	Intermediate Similarity	NPC475144
0.8057	Intermediate Similarity	NPC287243
0.8049	Intermediate Similarity	NPC471348
0.8049	Intermediate Similarity	NPC469416
0.8049	Intermediate Similarity	NPC228906
0.8049	Intermediate Similarity	NPC474305
0.8047	Intermediate Similarity	NPC313368
0.8047	Intermediate Similarity	NPC298093
0.8046	Intermediate Similarity	NPC157522
0.8046	Intermediate Similarity	NPC91650
0.8046	Intermediate Similarity	NPC473113
0.8038	Intermediate Similarity	NPC233707
0.8037	Intermediate Similarity	NPC19747
0.8037	Intermediate Similarity	NPC74539
0.8037	Intermediate Similarity	NPC304443
0.8036	Intermediate Similarity	NPC246647
0.8036	Intermediate Similarity	NPC473368
0.8036	Intermediate Similarity	NPC19600
0.8036	Intermediate Similarity	NPC123153
0.8036	Intermediate Similarity	NPC96342
0.8036	Intermediate Similarity	NPC212967
0.8036	Intermediate Similarity	NPC164110

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 NPC132054 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	387
0.1-0.2	997
0.2-0.3	1881
0.3-0.4	2686
0.4-0.5	1811
0.5-0.6	917
0.6-0.7	354
0.7-0.8	110
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.865	High Similarity	NPD919	Approved
0.8545	High Similarity	NPD1247	Approved
0.8129	Intermediate Similarity	NPD7473	Discontinued
0.8095	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD6232	Discontinued
0.8047	Intermediate Similarity	NPD5494	Approved
0.8037	Intermediate Similarity	NPD920	Approved
0.8024	Intermediate Similarity	NPD3817	Phase 2
0.8012	Intermediate Similarity	NPD3926	Phase 2
0.7914	Intermediate Similarity	NPD2533	Approved
0.7914	Intermediate Similarity	NPD2534	Approved
0.7914	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2532	Approved
0.7877	Intermediate Similarity	NPD8434	Phase 2
0.787	Intermediate Similarity	NPD3882	Suspended
0.7829	Intermediate Similarity	NPD5844	Phase 1
0.7791	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6599	Discontinued
0.7702	Intermediate Similarity	NPD1471	Phase 3
0.7702	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7819	Suspended
0.7647	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6799	Approved
0.7619	Intermediate Similarity	NPD3226	Approved
0.7607	Intermediate Similarity	NPD1243	Approved
0.7598	Intermediate Similarity	NPD6559	Discontinued
0.7571	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1934	Approved
0.7485	Intermediate Similarity	NPD6801	Discontinued
0.7485	Intermediate Similarity	NPD2346	Discontinued
0.7442	Intermediate Similarity	NPD2801	Approved
0.7421	Intermediate Similarity	NPD4107	Approved
0.7405	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD3818	Discontinued
0.7363	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6166	Phase 2
0.736	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5710	Approved
0.7345	Intermediate Similarity	NPD5711	Approved
0.7326	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD3749	Approved
0.7292	Intermediate Similarity	NPD4482	Phase 3
0.7289	Intermediate Similarity	NPD2800	Approved
0.7289	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6959	Discontinued
0.7288	Intermediate Similarity	NPD7199	Phase 2
0.7283	Intermediate Similarity	NPD37	Approved
0.7263	Intermediate Similarity	NPD2403	Approved
0.7257	Intermediate Similarity	NPD4966	Approved
0.7257	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4965	Approved
0.7257	Intermediate Similarity	NPD4967	Phase 2
0.7256	Intermediate Similarity	NPD3748	Approved
0.7256	Intermediate Similarity	NPD2799	Discontinued
0.7246	Intermediate Similarity	NPD4628	Phase 3
0.7243	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1465	Phase 2
0.7235	Intermediate Similarity	NPD1512	Approved
0.7229	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7411	Suspended
0.7222	Intermediate Similarity	NPD2979	Phase 3
0.7213	Intermediate Similarity	NPD6764	Approved
0.7213	Intermediate Similarity	NPD6765	Approved
0.7212	Intermediate Similarity	NPD2796	Approved
0.7212	Intermediate Similarity	NPD2438	Suspended
0.7205	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5402	Approved
0.7182	Intermediate Similarity	NPD3751	Discontinued
0.7178	Intermediate Similarity	NPD447	Suspended
0.7175	Intermediate Similarity	NPD6234	Discontinued
0.7174	Intermediate Similarity	NPD7808	Phase 3
0.7169	Intermediate Similarity	NPD2344	Approved
0.7158	Intermediate Similarity	NPD6797	Phase 2
0.7151	Intermediate Similarity	NPD7229	Phase 3
0.7151	Intermediate Similarity	NPD6808	Phase 2
0.712	Intermediate Similarity	NPD7251	Discontinued
0.7118	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1511	Approved
0.7117	Intermediate Similarity	NPD4060	Phase 1
0.7112	Intermediate Similarity	NPD8150	Discontinued
0.711	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2935	Discontinued
0.7104	Intermediate Similarity	NPD7074	Phase 3
0.7102	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD2163	Approved
0.7076	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1933	Approved
0.7073	Intermediate Similarity	NPD6355	Discontinued
0.7072	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1281	Approved
0.7065	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6785	Approved
0.7059	Intermediate Similarity	NPD6784	Approved
0.7056	Intermediate Similarity	NPD3787	Discontinued
0.7049	Intermediate Similarity	NPD7054	Approved
0.7049	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8312	Approved
0.7043	Intermediate Similarity	NPD8313	Approved
0.7041	Intermediate Similarity	NPD3750	Approved
0.7029	Intermediate Similarity	NPD6386	Approved
0.7029	Intermediate Similarity	NPD6385	Approved
0.7017	Intermediate Similarity	NPD5242	Approved
0.7011	Intermediate Similarity	NPD7472	Approved
0.701	Intermediate Similarity	NPD8285	Discontinued
0.7006	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1551	Phase 2
0.7005	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2309	Approved
0.6994	Remote Similarity	NPD5403	Approved
0.6994	Remote Similarity	NPD2313	Discontinued
0.699	Remote Similarity	NPD3057	Approved
0.6987	Remote Similarity	NPD5691	Approved
0.6977	Remote Similarity	NPD5401	Approved
0.6977	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3146	Approved
0.6975	Remote Similarity	NPD6832	Phase 2
0.6971	Remote Similarity	NPD4380	Phase 2
0.697	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7768	Phase 2
0.6954	Remote Similarity	NPD7435	Discontinued
0.6949	Remote Similarity	NPD5761	Phase 2
0.6949	Remote Similarity	NPD5760	Phase 2
0.6943	Remote Similarity	NPD17	Approved
0.6937	Remote Similarity	NPD1283	Approved
0.6914	Remote Similarity	NPD7458	Discontinued
0.691	Remote Similarity	NPD5353	Approved
0.6908	Remote Similarity	NPD7907	Approved
0.6906	Remote Similarity	NPD8127	Discontinued
0.6905	Remote Similarity	NPD2531	Phase 2
0.6904	Remote Similarity	NPD2972	Approved
0.6904	Remote Similarity	NPD3533	Approved
0.6902	Remote Similarity	NPD7228	Approved
0.6901	Remote Similarity	NPD3887	Approved
0.6894	Remote Similarity	NPD3267	Approved
0.6894	Remote Similarity	NPD3266	Approved
0.6893	Remote Similarity	NPD4665	Approved
0.6893	Remote Similarity	NPD6279	Approved
0.6893	Remote Similarity	NPD6280	Approved
0.6893	Remote Similarity	NPD4111	Phase 1
0.689	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1651	Approved
0.6878	Remote Similarity	NPD5980	Discovery
0.6864	Remote Similarity	NPD5762	Approved
0.6864	Remote Similarity	NPD5763	Approved
0.6864	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7003	Approved
0.6842	Remote Similarity	NPD4110	Phase 3
0.6839	Remote Similarity	NPD6273	Approved
0.6833	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1607	Approved
0.6824	Remote Similarity	NPD1549	Phase 2
0.6813	Remote Similarity	NPD1608	Approved
0.6811	Remote Similarity	NPD7177	Discontinued
0.6805	Remote Similarity	NPD5404	Approved
0.6805	Remote Similarity	NPD5406	Approved
0.6805	Remote Similarity	NPD5408	Approved
0.6805	Remote Similarity	NPD5405	Approved
0.6802	Remote Similarity	NPD6776	Approved
0.6802	Remote Similarity	NPD6777	Approved
0.6802	Remote Similarity	NPD6782	Approved
0.6802	Remote Similarity	NPD6781	Approved
0.6802	Remote Similarity	NPD6780	Approved
0.6802	Remote Similarity	NPD6778	Approved
0.6802	Remote Similarity	NPD6779	Approved
0.6802	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD8404	Phase 2
0.6791	Remote Similarity	NPD5953	Discontinued
0.6788	Remote Similarity	NPD6798	Discontinued
0.6788	Remote Similarity	NPD3268	Approved
0.6788	Remote Similarity	NPD7985	Registered
0.6786	Remote Similarity	NPD4420	Approved
0.6784	Remote Similarity	NPD6674	Discontinued
0.6772	Remote Similarity	NPD2968	Approved
0.6772	Remote Similarity	NPD2971	Approved
0.6766	Remote Similarity	NPD230	Phase 1
0.6765	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6002	Phase 3
0.6765	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6005	Phase 3
0.6765	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6004	Phase 3
0.6765	Remote Similarity	NPD2353	Approved
0.6755	Remote Similarity	NPD7240	Approved
0.675	Remote Similarity	NPD1611	Approved
0.675	Remote Similarity	NPD3705	Approved
0.6749	Remote Similarity	NPD7874	Approved
0.6749	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD8032	Phase 2
0.6746	Remote Similarity	NPD1509	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