NPASS Compound

Structure

CID269713 OpenBabel06191716072D 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 -4.3301 -2.5000 0.0000 Cl 0 0 0 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 -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 27 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 26 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:	438.25
Volume:	457.749
LogP:	3.554
LogD:	3.957
LogS:	-4.36
# Rotatable Bonds:	6
TPSA:	73.22
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.251
Synthetic Accessibility Score:	5.792
Fsp3:	0.76
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.485
MDCK Permeability:	3.57113967766054e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.938
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.28
Plasma Protein Binding (PPB):	95.77143096923828%
Volume Distribution (VD):	1.554
Pgp-substrate:	4.658529758453369%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.163
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.847
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.1
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.521
CYP3A4-inhibitor:	0.673
CYP3A4-substrate:	0.427

ADMET: Excretion

Clearance (CL):	6.476
Half-life (T1/2):	0.401

ADMET: Toxicity

hERG Blockers:	0.101
Human Hepatotoxicity (H-HT):	0.937
Drug-inuced Liver Injury (DILI):	0.849
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.248
Skin Sensitization:	0.119
Carcinogencity:	0.019
Eye Corrosion:	0.014
Eye Irritation:	0.041
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC269713

Natural Product ID:	NPC269713
*Common Name:**	Dehydroxychlorofusarielin B
IUPAC Name:	(2S,3S,4E,6E)-7-[(1aR,2R,3S,3aS,5R,6R,7aR,7bS)-2-[(E)-but-2-en-2-yl]-5-chloro-6-hydroxy-1a,6-dimethyl-2,3,3a,4,5,7,7a,7b-octahydronaphtho[1,2-b]oxiren-3-yl]-2,4-dimethylhepta-4,6-diene-1,3-diol
Synonyms:
Standard InCHIKey:	NUVPMECBNLBBBB-RGIDNKBKSA-N
Standard InCHI:	InChI=1S/C25H39ClO4/c1-7-14(2)21-17(10-8-9-15(3)22(28)16(4)13-27)18-11-20(26)24(5,29)12-19(18)23-25(21,6)30-23/h7-10,16-23,27-29H,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](Cl)[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:	CHEMBL426203
PubChem CID:	16756890
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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[568189]

☑ 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 NPC269713 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	241
0.1-0.2	1602
0.2-0.3	5303
0.3-0.4	14159
0.4-0.5	13187
0.5-0.6	6856
0.6-0.7	1313
0.7-0.8	33
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8421	Intermediate Similarity	NPC128066
0.8333	Intermediate Similarity	NPC191323
0.7455	Intermediate Similarity	NPC322912
0.7396	Intermediate Similarity	NPC476646
0.7327	Intermediate Similarity	NPC49783
0.7327	Intermediate Similarity	NPC16265
0.73	Intermediate Similarity	NPC477388
0.73	Intermediate Similarity	NPC477386
0.7292	Intermediate Similarity	NPC96362
0.7282	Intermediate Similarity	NPC119379
0.7273	Intermediate Similarity	NPC216636
0.7273	Intermediate Similarity	NPC319438
0.7238	Intermediate Similarity	NPC210717
0.7238	Intermediate Similarity	NPC103165
0.7216	Intermediate Similarity	NPC249423
0.72	Intermediate Similarity	NPC6391
0.72	Intermediate Similarity	NPC255143
0.72	Intermediate Similarity	NPC261266
0.7184	Intermediate Similarity	NPC97404
0.7184	Intermediate Similarity	NPC41554
0.717	Intermediate Similarity	NPC261807
0.7157	Intermediate Similarity	NPC115607
0.7143	Intermediate Similarity	NPC155521
0.7143	Intermediate Similarity	NPC259858
0.713	Intermediate Similarity	NPC476896
0.7128	Intermediate Similarity	NPC32832
0.7115	Intermediate Similarity	NPC310013
0.7103	Intermediate Similarity	NPC152480
0.7097	Intermediate Similarity	NPC220939
0.7097	Intermediate Similarity	NPC265485
0.7087	Intermediate Similarity	NPC291484
0.7087	Intermediate Similarity	NPC11216
0.7087	Intermediate Similarity	NPC295668
0.7087	Intermediate Similarity	NPC204188
0.7087	Intermediate Similarity	NPC3345
0.7087	Intermediate Similarity	NPC329596
0.7087	Intermediate Similarity	NPC80561
0.7083	Intermediate Similarity	NPC476314
0.7083	Intermediate Similarity	NPC13823
0.7083	Intermediate Similarity	NPC68119
0.7075	Intermediate Similarity	NPC288970
0.7075	Intermediate Similarity	NPC57664
0.7075	Intermediate Similarity	NPC72204
0.7053	Intermediate Similarity	NPC265588
0.7053	Intermediate Similarity	NPC63958
0.703	Intermediate Similarity	NPC153699
0.703	Intermediate Similarity	NPC281316
0.703	Intermediate Similarity	NPC76164
0.703	Intermediate Similarity	NPC299068
0.7021	Intermediate Similarity	NPC306727
0.7021	Intermediate Similarity	NPC201048
0.7021	Intermediate Similarity	NPC476366
0.7009	Intermediate Similarity	NPC476893
0.7	Intermediate Similarity	NPC102048
0.7	Intermediate Similarity	NPC83702
0.7	Intermediate Similarity	NPC205845
0.7	Intermediate Similarity	NPC474493
0.7	Intermediate Similarity	NPC474047
0.699	Remote Similarity	NPC97103
0.699	Remote Similarity	NPC470361
0.6989	Remote Similarity	NPC23954
0.6981	Remote Similarity	NPC276110
0.6981	Remote Similarity	NPC8774
0.6979	Remote Similarity	NPC470758
0.6979	Remote Similarity	NPC471798
0.6979	Remote Similarity	NPC91594
0.6979	Remote Similarity	NPC470711
0.6961	Remote Similarity	NPC476948
0.6961	Remote Similarity	NPC149224
0.6957	Remote Similarity	NPC304690
0.6957	Remote Similarity	NPC329989
0.6957	Remote Similarity	NPC239373
0.6957	Remote Similarity	NPC74722
0.6944	Remote Similarity	NPC476895
0.6944	Remote Similarity	NPC278673
0.6931	Remote Similarity	NPC470360
0.6931	Remote Similarity	NPC298595
0.6931	Remote Similarity	NPC164424
0.6916	Remote Similarity	NPC90583
0.6916	Remote Similarity	NPC12103
0.6916	Remote Similarity	NPC98457
0.6916	Remote Similarity	NPC227583
0.6915	Remote Similarity	NPC68443
0.6911	Remote Similarity	NPC156797
0.6911	Remote Similarity	NPC478207
0.6909	Remote Similarity	NPC109195
0.6909	Remote Similarity	NPC475038
0.6909	Remote Similarity	NPC470571
0.69	Remote Similarity	NPC237795
0.69	Remote Similarity	NPC475789
0.69	Remote Similarity	NPC477978
0.69	Remote Similarity	NPC82538
0.6893	Remote Similarity	NPC474668
0.6893	Remote Similarity	NPC67872
0.6893	Remote Similarity	NPC133588
0.6887	Remote Similarity	NPC65402
0.6887	Remote Similarity	NPC144202
0.6887	Remote Similarity	NPC127718
0.6881	Remote Similarity	NPC38855
0.6875	Remote Similarity	NPC253190
0.6875	Remote Similarity	NPC106432
0.6875	Remote Similarity	NPC470749
0.6869	Remote Similarity	NPC471270
0.6869	Remote Similarity	NPC320525
0.6863	Remote Similarity	NPC152808
0.6863	Remote Similarity	NPC139724
0.6863	Remote Similarity	NPC293287
0.686	Remote Similarity	NPC282003
0.686	Remote Similarity	NPC310035
0.686	Remote Similarity	NPC188222
0.6857	Remote Similarity	NPC275671
0.6857	Remote Similarity	NPC114389
0.6852	Remote Similarity	NPC218902
0.6852	Remote Similarity	NPC99726
0.6852	Remote Similarity	NPC125771
0.6832	Remote Similarity	NPC306951
0.6832	Remote Similarity	NPC238485
0.6832	Remote Similarity	NPC302360
0.6832	Remote Similarity	NPC231310
0.6827	Remote Similarity	NPC187785
0.6827	Remote Similarity	NPC477917
0.6827	Remote Similarity	NPC259875
0.6827	Remote Similarity	NPC101886
0.6822	Remote Similarity	NPC476894
0.6809	Remote Similarity	NPC167706
0.6804	Remote Similarity	NPC477427
0.6804	Remote Similarity	NPC474826
0.6804	Remote Similarity	NPC477426
0.6804	Remote Similarity	NPC476703
0.6804	Remote Similarity	NPC477425
0.6803	Remote Similarity	NPC303006
0.68	Remote Similarity	NPC50964
0.68	Remote Similarity	NPC477390
0.68	Remote Similarity	NPC49964
0.68	Remote Similarity	NPC218616
0.68	Remote Similarity	NPC477385
0.68	Remote Similarity	NPC296701
0.68	Remote Similarity	NPC101462
0.6796	Remote Similarity	NPC166857
0.6796	Remote Similarity	NPC189777
0.6792	Remote Similarity	NPC137461
0.6792	Remote Similarity	NPC27531
0.6774	Remote Similarity	NPC287903
0.6774	Remote Similarity	NPC234511
0.6771	Remote Similarity	NPC291503
0.6768	Remote Similarity	NPC471266
0.6768	Remote Similarity	NPC95124
0.6768	Remote Similarity	NPC287749
0.6768	Remote Similarity	NPC236707
0.6768	Remote Similarity	NPC324772
0.6765	Remote Similarity	NPC290731
0.6765	Remote Similarity	NPC474189
0.6765	Remote Similarity	NPC474349
0.6765	Remote Similarity	NPC266511
0.6765	Remote Similarity	NPC274448
0.6762	Remote Similarity	NPC192437
0.6762	Remote Similarity	NPC476226
0.6762	Remote Similarity	NPC14380
0.6762	Remote Similarity	NPC78973
0.6762	Remote Similarity	NPC220216
0.6762	Remote Similarity	NPC470390
0.6762	Remote Similarity	NPC77796
0.6762	Remote Similarity	NPC245410
0.6762	Remote Similarity	NPC270511
0.6762	Remote Similarity	NPC92885
0.6762	Remote Similarity	NPC48732
0.6759	Remote Similarity	NPC276103
0.6759	Remote Similarity	NPC54248
0.6757	Remote Similarity	NPC471889
0.6735	Remote Similarity	NPC83351
0.6735	Remote Similarity	NPC148977
0.6735	Remote Similarity	NPC52755
0.6735	Remote Similarity	NPC11908
0.6735	Remote Similarity	NPC167891
0.6733	Remote Similarity	NPC470384
0.6733	Remote Similarity	NPC320548
0.6733	Remote Similarity	NPC57370
0.6733	Remote Similarity	NPC185605
0.6733	Remote Similarity	NPC52108
0.6733	Remote Similarity	NPC476927
0.6733	Remote Similarity	NPC82623
0.6733	Remote Similarity	NPC474789
0.6731	Remote Similarity	NPC280556
0.6731	Remote Similarity	NPC470542
0.6731	Remote Similarity	NPC471952
0.6731	Remote Similarity	NPC475605
0.6731	Remote Similarity	NPC7280
0.6731	Remote Similarity	NPC229612
0.6731	Remote Similarity	NPC212596
0.6731	Remote Similarity	NPC4574
0.6729	Remote Similarity	NPC474690
0.6729	Remote Similarity	NPC105490
0.6701	Remote Similarity	NPC170148
0.67	Remote Similarity	NPC116202
0.67	Remote Similarity	NPC264245
0.67	Remote Similarity	NPC23852
0.67	Remote Similarity	NPC209620
0.6699	Remote Similarity	NPC201273
0.6699	Remote Similarity	NPC6605
0.6699	Remote Similarity	NPC476217

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 NPC269713 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	1638
0.2-0.3	4016
0.3-0.4	2381
0.4-0.5	657
0.5-0.6	214
0.6-0.7	40
0.7-0.8	0
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
0.7172	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6695	Phase 3
0.6796	Remote Similarity	NPD7750	Discontinued
0.6796	Remote Similarity	NPD7524	Approved
0.6768	Remote Similarity	NPD6931	Approved
0.6768	Remote Similarity	NPD7514	Phase 3
0.6768	Remote Similarity	NPD6930	Phase 2
0.6768	Remote Similarity	NPD7332	Phase 2
0.6727	Remote Similarity	NPD6648	Approved
0.67	Remote Similarity	NPD6902	Approved
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD6929	Approved
0.6612	Remote Similarity	NPD7101	Approved
0.6612	Remote Similarity	NPD7100	Approved
0.66	Remote Similarity	NPD7525	Registered
0.6598	Remote Similarity	NPD8264	Approved
0.6581	Remote Similarity	NPD5217	Approved
0.6581	Remote Similarity	NPD5216	Approved
0.6581	Remote Similarity	NPD5215	Approved
0.6566	Remote Similarity	NPD7145	Approved
0.6555	Remote Similarity	NPD5167	Approved
0.6542	Remote Similarity	NPD7087	Discontinued
0.65	Remote Similarity	NPD7645	Phase 2
0.6481	Remote Similarity	NPD5778	Approved
0.6481	Remote Similarity	NPD5779	Approved
0.6465	Remote Similarity	NPD6925	Approved
0.6465	Remote Similarity	NPD6932	Approved
0.6465	Remote Similarity	NPD5776	Phase 2
0.646	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6893	Approved
0.6429	Remote Similarity	NPD6336	Discontinued
0.64	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7637	Suspended
0.6373	Remote Similarity	NPD6898	Phase 1
0.6364	Remote Similarity	NPD6868	Approved
0.6327	Remote Similarity	NPD6924	Approved
0.6327	Remote Similarity	NPD6926	Approved
0.6325	Remote Similarity	NPD5168	Approved
0.6321	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7640	Approved
0.6283	Remote Similarity	NPD7639	Approved
0.6275	Remote Similarity	NPD7509	Discontinued
0.62	Remote Similarity	NPD6933	Approved
0.6195	Remote Similarity	NPD7638	Approved
0.6176	Remote Similarity	NPD6683	Phase 2
0.6147	Remote Similarity	NPD3168	Discontinued
0.6147	Remote Similarity	NPD7838	Discovery
0.6129	Remote Similarity	NPD6335	Approved
0.6122	Remote Similarity	NPD7151	Approved
0.6122	Remote Similarity	NPD7152	Approved
0.6122	Remote Similarity	NPD7150	Approved
0.61	Remote Similarity	NPD6942	Approved
0.61	Remote Similarity	NPD7339	Approved
0.6083	Remote Similarity	NPD5169	Approved
0.608	Remote Similarity	NPD4522	Approved
0.6053	Remote Similarity	NPD4225	Approved
0.6048	Remote Similarity	NPD7115	Discovery
0.604	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD5127	Approved
0.6022	Remote Similarity	NPD368	Approved
0.602	Remote Similarity	NPD7143	Approved
0.602	Remote Similarity	NPD7144	Approved
0.6018	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7136	Phase 2
0.6	Remote Similarity	NPD6314	Approved
0.6	Remote Similarity	NPD6313	Approved
0.5984	Remote Similarity	NPD5983	Phase 2
0.5918	Remote Similarity	NPD6923	Approved
0.5918	Remote Similarity	NPD6922	Approved
0.5909	Remote Similarity	NPD6101	Approved
0.5909	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4732	Discontinued
0.5897	Remote Similarity	NPD5211	Phase 2
0.5868	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD5956	Approved
0.5859	Remote Similarity	NPD7503	Approved
0.5833	Remote Similarity	NPD6033	Approved
0.5812	Remote Similarity	NPD4159	Approved
0.5806	Remote Similarity	NPD4632	Approved
0.5804	Remote Similarity	NPD7983	Approved
0.5804	Remote Similarity	NPD6411	Approved
0.5798	Remote Similarity	NPD5141	Approved
0.5785	Remote Similarity	NPD6881	Approved
0.5785	Remote Similarity	NPD5128	Approved
0.5785	Remote Similarity	NPD6899	Approved
0.5776	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD7632	Discontinued
0.5752	Remote Similarity	NPD6399	Phase 3
0.575	Remote Similarity	NPD6675	Approved
0.575	Remote Similarity	NPD7128	Approved
0.575	Remote Similarity	NPD5357	Phase 1
0.575	Remote Similarity	NPD6402	Approved
0.575	Remote Similarity	NPD6640	Phase 3
0.575	Remote Similarity	NPD5739	Approved
0.5748	Remote Similarity	NPD7327	Approved
0.5748	Remote Similarity	NPD7328	Approved
0.5741	Remote Similarity	NPD4786	Approved
0.5736	Remote Similarity	NPD8033	Approved
0.5726	Remote Similarity	NPD5286	Approved
0.5726	Remote Similarity	NPD5285	Approved
0.5726	Remote Similarity	NPD4696	Approved
0.5714	Remote Similarity	NPD6698	Approved
0.5714	Remote Similarity	NPD46	Approved
0.5703	Remote Similarity	NPD7516	Approved
0.5702	Remote Similarity	NPD7748	Approved
0.5702	Remote Similarity	NPD5697	Approved
0.5701	Remote Similarity	NPD3667	Approved
0.5691	Remote Similarity	NPD7102	Approved
0.5691	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD6883	Approved
0.5691	Remote Similarity	NPD7290	Approved
0.569	Remote Similarity	NPD4755	Approved
0.569	Remote Similarity	NPD7902	Approved
0.5686	Remote Similarity	NPD4784	Approved
0.5686	Remote Similarity	NPD4785	Approved
0.5669	Remote Similarity	NPD6009	Approved
0.5664	Remote Similarity	NPD6079	Approved
0.5664	Remote Similarity	NPD7515	Phase 2
0.566	Remote Similarity	NPD4822	Approved
0.566	Remote Similarity	NPD4819	Approved
0.566	Remote Similarity	NPD4820	Approved
0.566	Remote Similarity	NPD4821	Approved
0.566	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD8377	Approved
0.5659	Remote Similarity	NPD7741	Discontinued
0.5659	Remote Similarity	NPD8294	Approved
0.5656	Remote Similarity	NPD7320	Approved
0.5645	Remote Similarity	NPD6869	Approved
0.5645	Remote Similarity	NPD6847	Approved
0.5645	Remote Similarity	NPD8130	Phase 1
0.5645	Remote Similarity	NPD6649	Approved
0.5645	Remote Similarity	NPD6617	Approved
0.5645	Remote Similarity	NPD6650	Approved
0.5636	Remote Similarity	NPD3618	Phase 1
0.563	Remote Similarity	NPD5224	Approved
0.563	Remote Similarity	NPD5226	Approved
0.563	Remote Similarity	NPD4633	Approved
0.563	Remote Similarity	NPD5225	Approved
0.5625	Remote Similarity	NPD5328	Approved
0.562	Remote Similarity	NPD6008	Approved
0.5615	Remote Similarity	NPD8516	Approved
0.5615	Remote Similarity	NPD8517	Approved
0.5615	Remote Similarity	NPD8378	Approved
0.5615	Remote Similarity	NPD8380	Approved
0.5615	Remote Similarity	NPD8296	Approved
0.5615	Remote Similarity	NPD8513	Phase 3
0.5615	Remote Similarity	NPD8379	Approved
0.5615	Remote Similarity	NPD8515	Approved
0.5615	Remote Similarity	NPD8335	Approved
0.5614	Remote Similarity	NPD4202	Approved
0.561	Remote Similarity	NPD6012	Approved
0.561	Remote Similarity	NPD6014	Approved
0.561	Remote Similarity	NPD6372	Approved
0.561	Remote Similarity	NPD6013	Approved
0.561	Remote Similarity	NPD6373	Approved
0.5603	Remote Similarity	NPD7839	Suspended
0.56	Remote Similarity	NPD8297	Approved
0.56	Remote Similarity	NPD6882	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