NPASS Compound

Structure

CID191323 OpenBabel06191715572D 30 32 0 0 1 0 0 0 0 0999 V2000 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -7.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -6.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -0.1340 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 7 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 7 14 2 0 0 0 0 8 9 1 0 0 0 0 8 10 2 0 0 0 0 9 15 2 0 0 0 0 11 20 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 26 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 4 1 1 0 0 0 16 22 1 0 0 0 0 17 10 1 1 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 11 1 6 0 0 0 18 19 1 0 0 0 0 19 12 1 1 0 0 0 19 23 1 0 0 0 0 20 24 1 1 0 0 0 20 27 1 0 0 0 0 21 25 1 1 0 0 0 22 28 1 6 0 0 0 23 25 1 1 0 0 0 23 30 1 0 0 0 0 24 5 1 1 0 0 0 24 29 1 0 0 0 0 25 6 1 1 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.29
Volume:	451.328
LogP:	2.319
LogD:	2.713
LogS:	-3.928
# Rotatable Bonds:	6
TPSA:	93.45
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.301
Synthetic Accessibility Score:	5.681
Fsp3:	0.76
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:	-4.826
MDCK Permeability:	0.00015461136354133487
Pgp-inhibitor:	0.001
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.06
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.113

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.275
Plasma Protein Binding (PPB):	87.25088500976562%
Volume Distribution (VD):	1.049
Pgp-substrate:	7.979744911193848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.784
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.101
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.267
CYP3A4-inhibitor:	0.255
CYP3A4-substrate:	0.343

ADMET: Excretion

Clearance (CL):	6.173
Half-life (T1/2):	0.54

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.921
Drug-inuced Liver Injury (DILI):	0.817
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.558
Maximum Recommended Daily Dose:	0.587
Skin Sensitization:	0.163
Carcinogencity:	0.013
Eye Corrosion:	0.007
Eye Irritation:	0.045
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC191323

Natural Product ID:	NPC191323
*Common Name:**	Fusarielin B
IUPAC Name:	(1aR,2R,3S,3aS,5R,6R,7aR,7bS)-2-[(E)-but-2-en-2-yl]-3-[(1E,3E,5S,6S)-5,7-dihydroxy-4,6-dimethylhepta-1,3-dienyl]-1a,6-dimethyl-2,3,3a,4,5,7,7a,7b-octahydronaphtho[1,2-b]oxirene-5,6-diol
Synonyms:
Standard InCHIKey:	NJULGUREPHOGBR-RGIDNKBKSA-N
Standard InCHI:	InChI=1S/C25H40O5/c1-7-14(2)21-17(10-8-9-15(3)22(28)16(4)13-26)18-11-20(27)24(5,29)12-19(18)23-25(21,6)30-23/h7-10,16-23,26-29H,11-13H2,1-6H3/b10-8+,14-7+,15-9+/t16-,17-,18-,19+,20+,21-,22+,23-,24+,25+/m0/s1
SMILES:	OC[C@@H]([C@@H](/C(=C/C=C/[C@H]1[C@@H]2C[C@@H](O)[C@](C[C@H]2[C@H]2[C@]([C@H]1/C(=C/C)/C)(C)O2)(C)O)/C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228495
PubChem CID:	10432292
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	rhizosphere	Sonoran desert	n.a.	PMID[15620238]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17542490]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17564467]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053517]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21366228]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	healthy leaf of Ginkgo biloba	campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	isolated from the sponge Xestospongia testudinaria	n.a.	n.a.	PMID[22225637]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	Isolated from a sandy-loam soil sample	50 m inland from Waikiki Beach, Honolulu, Hawaii	2010-JUL	PMID[22400916]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22703109]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23527875]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24050204]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25001296]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25581396]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26273902]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31012585]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33305943]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19704	Caulerpa trifaria	Species	Caulerpaceae	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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	62.5	ug.mL-1	PMID[538210]

☑ 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 NPC191323 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	211
0.1-0.2	1384
0.2-0.3	4344
0.3-0.4	8257
0.4-0.5	15341
0.5-0.6	8354
0.6-0.7	4220
0.7-0.8	563
0.8-0.85	20
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9419	High Similarity	NPC128066
0.8681	High Similarity	NPC119379
0.8602	High Similarity	NPC210717
0.8602	High Similarity	NPC103165
0.8404	Intermediate Similarity	NPC72204
0.8352	Intermediate Similarity	NPC49783
0.8352	Intermediate Similarity	NPC115607
0.8333	Intermediate Similarity	NPC269713
0.8316	Intermediate Similarity	NPC261807
0.8315	Intermediate Similarity	NPC298595
0.8295	Intermediate Similarity	NPC477978
0.8222	Intermediate Similarity	NPC255143
0.8202	Intermediate Similarity	NPC83702
0.8172	Intermediate Similarity	NPC114389
0.8172	Intermediate Similarity	NPC41554
0.8172	Intermediate Similarity	NPC97404
0.8152	Intermediate Similarity	NPC97103
0.814	Intermediate Similarity	NPC52755
0.814	Intermediate Similarity	NPC68119
0.814	Intermediate Similarity	NPC13823
0.8132	Intermediate Similarity	NPC476948
0.8085	Intermediate Similarity	NPC310013
0.8068	Intermediate Similarity	NPC476646
0.8068	Intermediate Similarity	NPC471270
0.8065	Intermediate Similarity	NPC329596
0.8065	Intermediate Similarity	NPC3345
0.8065	Intermediate Similarity	NPC204188
0.8065	Intermediate Similarity	NPC291484
0.8065	Intermediate Similarity	NPC11216
0.8065	Intermediate Similarity	NPC80561
0.8061	Intermediate Similarity	NPC476896
0.8043	Intermediate Similarity	NPC133588
0.8043	Intermediate Similarity	NPC474668
0.8022	Intermediate Similarity	NPC281316
0.8021	Intermediate Similarity	NPC57664
0.8021	Intermediate Similarity	NPC90583
0.8021	Intermediate Similarity	NPC288970
0.798	Intermediate Similarity	NPC470571
0.7979	Intermediate Similarity	NPC275671
0.7957	Intermediate Similarity	NPC470361
0.7957	Intermediate Similarity	NPC187785
0.7957	Intermediate Similarity	NPC259875
0.7957	Intermediate Similarity	NPC16265
0.7955	Intermediate Similarity	NPC471266
0.7955	Intermediate Similarity	NPC96362
0.7955	Intermediate Similarity	NPC287749
0.7955	Intermediate Similarity	NPC236707
0.7955	Intermediate Similarity	NPC95124
0.7938	Intermediate Similarity	NPC476021
0.7938	Intermediate Similarity	NPC476040
0.7938	Intermediate Similarity	NPC476893
0.7938	Intermediate Similarity	NPC474994
0.7935	Intermediate Similarity	NPC189777
0.7917	Intermediate Similarity	NPC8774
0.7912	Intermediate Similarity	NPC290731
0.7895	Intermediate Similarity	NPC137461
0.7889	Intermediate Similarity	NPC185605
0.7872	Intermediate Similarity	NPC295668
0.7865	Intermediate Similarity	NPC249423
0.7857	Intermediate Similarity	NPC476895
0.7849	Intermediate Similarity	NPC280556
0.7849	Intermediate Similarity	NPC67872
0.7835	Intermediate Similarity	NPC12103
0.7835	Intermediate Similarity	NPC227583
0.7835	Intermediate Similarity	NPC98457
0.7826	Intermediate Similarity	NPC261266
0.7826	Intermediate Similarity	NPC237344
0.7826	Intermediate Similarity	NPC6391
0.7826	Intermediate Similarity	NPC476217
0.7816	Intermediate Similarity	NPC476703
0.7812	Intermediate Similarity	NPC65402
0.7812	Intermediate Similarity	NPC127718
0.7802	Intermediate Similarity	NPC102048
0.78	Intermediate Similarity	NPC11956
0.7791	Intermediate Similarity	NPC32832
0.7789	Intermediate Similarity	NPC210268
0.7778	Intermediate Similarity	NPC155521
0.7778	Intermediate Similarity	NPC477390
0.7778	Intermediate Similarity	NPC477385
0.7778	Intermediate Similarity	NPC38855
0.7778	Intermediate Similarity	NPC259858
0.7766	Intermediate Similarity	NPC161560
0.7765	Intermediate Similarity	NPC220939
0.7765	Intermediate Similarity	NPC265485
0.7755	Intermediate Similarity	NPC26307
0.7755	Intermediate Similarity	NPC240372
0.7755	Intermediate Similarity	NPC120446
0.7742	Intermediate Similarity	NPC233744
0.7742	Intermediate Similarity	NPC470620
0.7732	Intermediate Similarity	NPC476894
0.7727	Intermediate Similarity	NPC83351
0.7727	Intermediate Similarity	NPC476314
0.7727	Intermediate Similarity	NPC477089
0.7727	Intermediate Similarity	NPC167891
0.7723	Intermediate Similarity	NPC23584
0.7701	Intermediate Similarity	NPC265588
0.7701	Intermediate Similarity	NPC63958
0.7701	Intermediate Similarity	NPC170148
0.77	Intermediate Similarity	NPC235920
0.77	Intermediate Similarity	NPC96784
0.77	Intermediate Similarity	NPC475617
0.7692	Intermediate Similarity	NPC320548
0.7684	Intermediate Similarity	NPC473956
0.7684	Intermediate Similarity	NPC475751
0.7677	Intermediate Similarity	NPC247233
0.7677	Intermediate Similarity	NPC312325
0.7674	Intermediate Similarity	NPC201048
0.7674	Intermediate Similarity	NPC24590
0.7674	Intermediate Similarity	NPC306727
0.7674	Intermediate Similarity	NPC476366
0.766	Intermediate Similarity	NPC475664
0.7653	Intermediate Similarity	NPC471903
0.7647	Intermediate Similarity	NPC473543
0.7647	Intermediate Similarity	NPC23954
0.7647	Intermediate Similarity	NPC242992
0.764	Intermediate Similarity	NPC72755
0.764	Intermediate Similarity	NPC476367
0.7634	Intermediate Similarity	NPC299068
0.7634	Intermediate Similarity	NPC94462
0.7634	Intermediate Similarity	NPC475069
0.7634	Intermediate Similarity	NPC125399
0.7634	Intermediate Similarity	NPC175145
0.7629	Intermediate Similarity	NPC469491
0.7629	Intermediate Similarity	NPC144202
0.7629	Intermediate Similarity	NPC305160
0.7624	Intermediate Similarity	NPC470972
0.7624	Intermediate Similarity	NPC109195
0.7624	Intermediate Similarity	NPC475038
0.7619	Intermediate Similarity	NPC177047
0.7619	Intermediate Similarity	NPC239373
0.7619	Intermediate Similarity	NPC304690
0.7619	Intermediate Similarity	NPC329989
0.7619	Intermediate Similarity	NPC74722
0.7614	Intermediate Similarity	NPC477924
0.7614	Intermediate Similarity	NPC130136
0.7614	Intermediate Similarity	NPC91594
0.7614	Intermediate Similarity	NPC471798
0.7614	Intermediate Similarity	NPC470758
0.7614	Intermediate Similarity	NPC470711
0.7609	Intermediate Similarity	NPC238992
0.7609	Intermediate Similarity	NPC474047
0.7609	Intermediate Similarity	NPC205845
0.7609	Intermediate Similarity	NPC474493
0.7609	Intermediate Similarity	NPC185568
0.7604	Intermediate Similarity	NPC91251
0.7604	Intermediate Similarity	NPC302584
0.76	Intermediate Similarity	NPC64348
0.76	Intermediate Similarity	NPC474571
0.76	Intermediate Similarity	NPC254567
0.76	Intermediate Similarity	NPC272223
0.76	Intermediate Similarity	NPC79303
0.7596	Intermediate Similarity	NPC472218
0.7596	Intermediate Similarity	NPC472217
0.7596	Intermediate Similarity	NPC472219
0.7596	Intermediate Similarity	NPC311223
0.7596	Intermediate Similarity	NPC50124
0.7582	Intermediate Similarity	NPC471408
0.7579	Intermediate Similarity	NPC246028
0.7579	Intermediate Similarity	NPC109744
0.7579	Intermediate Similarity	NPC477917
0.7576	Intermediate Similarity	NPC474785
0.7576	Intermediate Similarity	NPC473244
0.7576	Intermediate Similarity	NPC316604
0.7576	Intermediate Similarity	NPC474938
0.7576	Intermediate Similarity	NPC477226
0.7573	Intermediate Similarity	NPC472898
0.7573	Intermediate Similarity	NPC472900
0.7573	Intermediate Similarity	NPC472899
0.7558	Intermediate Similarity	NPC68443
0.7558	Intermediate Similarity	NPC95165
0.7553	Intermediate Similarity	NPC474657
0.7553	Intermediate Similarity	NPC186145
0.7553	Intermediate Similarity	NPC149224
0.7553	Intermediate Similarity	NPC245004
0.7551	Intermediate Similarity	NPC476720
0.7551	Intermediate Similarity	NPC276110
0.7549	Intermediate Similarity	NPC473129
0.7549	Intermediate Similarity	NPC473523
0.7549	Intermediate Similarity	NPC474124
0.7549	Intermediate Similarity	NPC99627
0.7527	Intermediate Similarity	NPC470360
0.7527	Intermediate Similarity	NPC164424
0.7526	Intermediate Similarity	NPC27531
0.7525	Intermediate Similarity	NPC476897
0.7525	Intermediate Similarity	NPC472554
0.7525	Intermediate Similarity	NPC11974
0.7524	Intermediate Similarity	NPC87335
0.7524	Intermediate Similarity	NPC316974
0.7524	Intermediate Similarity	NPC472901
0.75	Intermediate Similarity	NPC477875
0.75	Intermediate Similarity	NPC159168
0.75	Intermediate Similarity	NPC220216
0.75	Intermediate Similarity	NPC317458
0.75	Intermediate Similarity	NPC125423
0.75	Intermediate Similarity	NPC475789
0.75	Intermediate Similarity	NPC278673
0.75	Intermediate Similarity	NPC82538
0.75	Intermediate Similarity	NPC48732
0.75	Intermediate Similarity	NPC253190
0.75	Intermediate Similarity	NPC471987

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 NPC191323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1479
0.2-0.3	3790
0.3-0.4	2277
0.4-0.5	1034
0.5-0.6	291
0.6-0.7	73
0.7-0.8	11
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
0.7935	Intermediate Similarity	NPD7524	Approved
0.7879	Intermediate Similarity	NPD5344	Discontinued
0.7802	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6648	Approved
0.7692	Intermediate Similarity	NPD6695	Phase 3
0.7368	Intermediate Similarity	NPD7750	Discontinued
0.7363	Intermediate Similarity	NPD6930	Phase 2
0.7363	Intermediate Similarity	NPD7332	Phase 2
0.7363	Intermediate Similarity	NPD6931	Approved
0.7363	Intermediate Similarity	NPD7514	Phase 3
0.7283	Intermediate Similarity	NPD6902	Approved
0.7253	Intermediate Similarity	NPD6929	Approved
0.7191	Intermediate Similarity	NPD8264	Approved
0.7174	Intermediate Similarity	NPD7525	Registered
0.7143	Intermediate Similarity	NPD7838	Discovery
0.7143	Intermediate Similarity	NPD7145	Approved
0.7143	Intermediate Similarity	NPD3168	Discontinued
0.7111	Intermediate Similarity	NPD6933	Approved
0.7071	Intermediate Similarity	NPD7087	Discontinued
0.7065	Intermediate Similarity	NPD7645	Phase 2
0.7033	Intermediate Similarity	NPD6925	Approved
0.7033	Intermediate Similarity	NPD6932	Approved
0.7033	Intermediate Similarity	NPD5776	Phase 2
0.7	Intermediate Similarity	NPD5779	Approved
0.7	Intermediate Similarity	NPD5778	Approved
0.6979	Remote Similarity	NPD6893	Approved
0.6957	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7640	Approved
0.6923	Remote Similarity	NPD7639	Approved
0.6915	Remote Similarity	NPD6898	Phase 1
0.69	Remote Similarity	NPD7637	Suspended
0.6889	Remote Similarity	NPD6924	Approved
0.6889	Remote Similarity	NPD6926	Approved
0.6881	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7638	Approved
0.6827	Remote Similarity	NPD4225	Approved
0.6809	Remote Similarity	NPD7509	Discontinued
0.6754	Remote Similarity	NPD7115	Discovery
0.6733	Remote Similarity	NPD7983	Approved
0.6702	Remote Similarity	NPD6683	Phase 2
0.6698	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD7150	Approved
0.6667	Remote Similarity	NPD7151	Approved
0.6667	Remote Similarity	NPD7152	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6638	Remote Similarity	NPD7516	Approved
0.6634	Remote Similarity	NPD6698	Approved
0.6634	Remote Similarity	NPD46	Approved
0.663	Remote Similarity	NPD6942	Approved
0.663	Remote Similarity	NPD7339	Approved
0.6606	Remote Similarity	NPD5357	Phase 1
0.6588	Remote Similarity	NPD368	Approved
0.6559	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7143	Approved
0.6556	Remote Similarity	NPD7144	Approved
0.6552	Remote Similarity	NPD7327	Approved
0.6552	Remote Similarity	NPD7328	Approved
0.6525	Remote Similarity	NPD8033	Approved
0.6518	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7136	Phase 2
0.6455	Remote Similarity	NPD6640	Phase 3
0.6444	Remote Similarity	NPD6923	Approved
0.6444	Remote Similarity	NPD6922	Approved
0.6441	Remote Similarity	NPD8377	Approved
0.6441	Remote Similarity	NPD8294	Approved
0.6437	Remote Similarity	NPD371	Approved
0.6413	Remote Similarity	NPD4732	Discontinued
0.6387	Remote Similarity	NPD8380	Approved
0.6387	Remote Similarity	NPD8296	Approved
0.6387	Remote Similarity	NPD8379	Approved
0.6387	Remote Similarity	NPD8335	Approved
0.6387	Remote Similarity	NPD8378	Approved
0.6387	Remote Similarity	NPD8517	Approved
0.6387	Remote Similarity	NPD8513	Phase 3
0.6387	Remote Similarity	NPD8515	Approved
0.6387	Remote Similarity	NPD8516	Approved
0.6373	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6101	Approved
0.6339	Remote Similarity	NPD6686	Approved
0.633	Remote Similarity	NPD7632	Discontinued
0.633	Remote Similarity	NPD5211	Phase 2
0.6283	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD6412	Phase 2
0.625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4634	Approved
0.6216	Remote Similarity	NPD5141	Approved
0.6207	Remote Similarity	NPD4632	Approved
0.62	Remote Similarity	NPD4786	Approved
0.6195	Remote Similarity	NPD6881	Approved
0.6195	Remote Similarity	NPD6899	Approved
0.619	Remote Similarity	NPD6399	Phase 3
0.6179	Remote Similarity	NPD7507	Approved
0.6176	Remote Similarity	NPD4250	Approved
0.6176	Remote Similarity	NPD4251	Approved
0.617	Remote Similarity	NPD4784	Approved
0.617	Remote Similarity	NPD4785	Approved
0.6167	Remote Similarity	NPD7741	Discontinued
0.6167	Remote Similarity	NPD6054	Approved
0.6167	Remote Similarity	NPD6319	Approved
0.6162	Remote Similarity	NPD3667	Approved
0.6161	Remote Similarity	NPD7128	Approved
0.6161	Remote Similarity	NPD6008	Approved
0.6161	Remote Similarity	NPD6675	Approved
0.6161	Remote Similarity	NPD5739	Approved
0.6161	Remote Similarity	NPD6402	Approved
0.6147	Remote Similarity	NPD5286	Approved
0.6147	Remote Similarity	NPD5285	Approved
0.6147	Remote Similarity	NPD4696	Approved
0.6132	Remote Similarity	NPD7748	Approved
0.6129	Remote Similarity	NPD8074	Phase 3
0.6122	Remote Similarity	NPD4820	Approved
0.6122	Remote Similarity	NPD4819	Approved
0.6122	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4821	Approved
0.6122	Remote Similarity	NPD4822	Approved
0.6121	Remote Similarity	NPD8297	Approved
0.6111	Remote Similarity	NPD7902	Approved
0.6111	Remote Similarity	NPD4755	Approved
0.6106	Remote Similarity	NPD5697	Approved
0.6095	Remote Similarity	NPD6079	Approved
0.6095	Remote Similarity	NPD7515	Phase 2
0.6087	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7102	Approved
0.6087	Remote Similarity	NPD7290	Approved
0.6087	Remote Similarity	NPD6883	Approved
0.6078	Remote Similarity	NPD4249	Approved
0.6078	Remote Similarity	NPD3618	Phase 1
0.6066	Remote Similarity	NPD5125	Phase 3
0.6066	Remote Similarity	NPD5126	Approved
0.6066	Remote Similarity	NPD6370	Approved
0.6058	Remote Similarity	NPD5328	Approved
0.6053	Remote Similarity	NPD7320	Approved
0.6038	Remote Similarity	NPD4202	Approved
0.6036	Remote Similarity	NPD5224	Approved
0.6036	Remote Similarity	NPD5226	Approved
0.6036	Remote Similarity	NPD4633	Approved
0.6036	Remote Similarity	NPD5225	Approved
0.6034	Remote Similarity	NPD6847	Approved
0.6034	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD8130	Phase 1
0.6034	Remote Similarity	NPD6650	Approved
0.6034	Remote Similarity	NPD6869	Approved
0.6034	Remote Similarity	NPD6617	Approved
0.6034	Remote Similarity	NPD6649	Approved
0.6033	Remote Similarity	NPD6059	Approved
0.6032	Remote Similarity	NPD7319	Approved
0.6019	Remote Similarity	NPD7839	Suspended
0.6017	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD6012	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5984	Remote Similarity	NPD6015	Approved
0.5984	Remote Similarity	NPD6016	Approved
0.5983	Remote Similarity	NPD6053	Discontinued
0.5983	Remote Similarity	NPD6882	Approved
0.5982	Remote Similarity	NPD5175	Approved
0.5982	Remote Similarity	NPD5174	Approved
0.598	Remote Similarity	NPD1696	Phase 3
0.5968	Remote Similarity	NPD7492	Approved
0.5965	Remote Similarity	NPD5701	Approved
0.596	Remote Similarity	NPD4748	Discontinued
0.5957	Remote Similarity	NPD4243	Approved
0.5948	Remote Similarity	NPD6371	Approved
0.5946	Remote Similarity	NPD5223	Approved
0.5941	Remote Similarity	NPD7154	Phase 3
0.5941	Remote Similarity	NPD6110	Phase 1
0.5935	Remote Similarity	NPD5988	Approved
0.5932	Remote Similarity	NPD8133	Approved
0.592	Remote Similarity	NPD6616	Approved
0.5918	Remote Similarity	NPD4271	Approved
0.5918	Remote Similarity	NPD4268	Approved
0.5917	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6009	Approved
0.5913	Remote Similarity	NPD6011	Approved
0.5905	Remote Similarity	NPD6051	Approved
0.5887	Remote Similarity	NPD8328	Phase 3
0.5882	Remote Similarity	NPD342	Phase 1
0.5873	Remote Similarity	NPD7078	Approved
0.5872	Remote Similarity	NPD5221	Approved
0.5872	Remote Similarity	NPD5222	Approved
0.5872	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.587	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD5983	Phase 2
0.5854	Remote Similarity	NPD6921	Approved
0.5851	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5282	Discontinued
0.5833	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7900	Approved
0.5827	Remote Similarity	NPD7736	Approved
0.5818	Remote Similarity	NPD5173	Approved
0.5818	Remote Similarity	NPD6084	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data