NPASS Compound

Structure

CID245320 OpenBabel06191716042D 30 33 0 0 1 0 0 0 0 0999 V2000 -5.9539 -0.3620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2064 -1.3715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6671 0.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3658 0.0183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8328 0.5192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9542 -1.3711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0807 -2.8849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2069 -3.3897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3327 -1.9236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6670 -2.8858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0804 -1.8758 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6669 -0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4997 -0.4815 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3329 -2.8854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4996 -1.4429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6667 -1.9240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8332 -1.4432 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8331 -1.4435 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4994 -0.4805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6664 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6665 -1.9247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8330 -0.4808 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8333 -0.4811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3653 0.0197 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.6663 1.0003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6664 -2.9247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8335 0.5189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5001 -3.3665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4995 -1.4439 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 6 1 0 0 0 0 3 12 1 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 14 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 10 28 1 0 0 0 0 11 2 1 6 0 0 0 12 13 1 0 0 0 0 12 23 1 6 0 0 0 13 4 1 1 0 0 0 13 29 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 1 0 0 0 18 21 1 0 0 0 0 18 23 1 6 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 22 1 0 0 0 0 20 25 2 0 0 0 0 21 26 2 0 0 0 0 21 29 1 0 0 0 0 22 5 1 6 0 0 0 22 30 1 0 0 0 0 23 27 1 1 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.15
Volume:	424.272
LogP:	4.833
LogD:	3.718
LogS:	-5.156
# Rotatable Bonds:	3
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.681
Synthetic Accessibility Score:	5.492
Fsp3:	0.565
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.612
MDCK Permeability:	1.4032876606506761e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.12
30% Bioavailability (F30%):	0.907

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.99
Plasma Protein Binding (PPB):	78.01002502441406%
Volume Distribution (VD):	2.427
Pgp-substrate:	17.309158325195312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.933
CYP1A2-substrate:	0.472
CYP2C19-inhibitor:	0.807
CYP2C19-substrate:	0.721
CYP2C9-inhibitor:	0.717
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.716
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.939
CYP3A4-substrate:	0.511

ADMET: Excretion

Clearance (CL):	6.365
Half-life (T1/2):	0.061

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.309
Rat Oral Acute Toxicity:	0.858
Maximum Recommended Daily Dose:	0.871
Skin Sensitization:	0.927
Carcinogencity:	0.843
Eye Corrosion:	0.018
Eye Irritation:	0.055
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC245320

Natural Product ID:	NPC245320
*Common Name:**	Chaetomugilin D
IUPAC Name:	n.a.
Synonyms:	Chaetomugilin D
Standard InCHIKey:	VFAOIGZBHFMFIU-XSKLMDGHSA-N
Standard InCHI:	InChI=1S/C23H27ClO6/c1-6-11(2)7-8-14-9-15-16(10-28-14)17-18-21(26)29-13(4)12(3)23(18,27)30-22(17,5)20(25)19(15)24/h7-13,17-18,27H,6H2,1-5H3/b8-7+/t11-,12+,13+,17+,18-,22-,23+/m0/s1
SMILES:	CC[C@@H](/C=C/C1=CC2=C(Cl)C(=O)[C@@]3([C@H](C2=CO1)[C@H]1C(=O)O[C@@H]([C@H]([C@]1(O3)O)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494745
PubChem CID:	25148534
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12357398]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12483566]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497948]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921417]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209910]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499339]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872138]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16904330]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125234]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827664]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19427327]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20225834]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20814854]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	isolated from the leaves of Viguiera robusta	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21640594]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854043]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22112725]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22593034]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23072467]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	Xichang of Sichuan Province, China	n.a.	PMID[26125976]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26343828]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5066072]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7116505]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	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	1
Others	5

Activity Type	# Activity
Cell Line	4
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	100.0	%	PMID[496642]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	68.2	%	PMID[496642]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	85.3	%	PMID[496642]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	28100.0	nM	PMID[496642]
NPT176	Organism	Artemia salina	Artemia salina	Activity	=	75.2	%	PMID[496641]
NPT2	Others	Unspecified		Inhibition	=	28.2	%	PMID[496642]

☑ 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 NPC245320 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	1133
0.2-0.3	3999
0.3-0.4	8647
0.4-0.5	15014
0.5-0.6	9516
0.6-0.7	3915
0.7-0.8	251
0.8-0.85	6
0.85-0.9	0
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9909	High Similarity	NPC473145
0.9909	High Similarity	NPC31641
0.9636	High Similarity	NPC243298
0.9554	High Similarity	NPC476815
0.8545	High Similarity	NPC473144
0.8545	High Similarity	NPC297281
0.8468	Intermediate Similarity	NPC272528
0.8378	Intermediate Similarity	NPC271059
0.8378	Intermediate Similarity	NPC25666
0.8108	Intermediate Similarity	NPC215253
0.8108	Intermediate Similarity	NPC185253
0.8091	Intermediate Similarity	NPC134083
0.8036	Intermediate Similarity	NPC469851
0.8018	Intermediate Similarity	NPC166770
0.8017	Intermediate Similarity	NPC23497
0.8	Intermediate Similarity	NPC232969
0.8	Intermediate Similarity	NPC199107
0.7909	Intermediate Similarity	NPC31021
0.7759	Intermediate Similarity	NPC469852
0.775	Intermediate Similarity	NPC326264
0.7719	Intermediate Similarity	NPC469657
0.7719	Intermediate Similarity	NPC244456
0.7719	Intermediate Similarity	NPC224172
0.7692	Intermediate Similarity	NPC469853
0.7658	Intermediate Similarity	NPC143210
0.7603	Intermediate Similarity	NPC321496
0.7589	Intermediate Similarity	NPC12727
0.7563	Intermediate Similarity	NPC220705
0.7521	Intermediate Similarity	NPC66108
0.7477	Intermediate Similarity	NPC166110
0.7458	Intermediate Similarity	NPC472645
0.7442	Intermediate Similarity	NPC476008
0.744	Intermediate Similarity	NPC268958
0.744	Intermediate Similarity	NPC158963
0.7422	Intermediate Similarity	NPC24651
0.7414	Intermediate Similarity	NPC472643
0.7411	Intermediate Similarity	NPC248193
0.7402	Intermediate Similarity	NPC312833
0.7387	Intermediate Similarity	NPC224270
0.7373	Intermediate Similarity	NPC474898
0.7368	Intermediate Similarity	NPC318082
0.7364	Intermediate Similarity	NPC477745
0.7355	Intermediate Similarity	NPC89408
0.7355	Intermediate Similarity	NPC478209
0.735	Intermediate Similarity	NPC235369
0.7344	Intermediate Similarity	NPC18945
0.7344	Intermediate Similarity	NPC105926
0.7344	Intermediate Similarity	NPC265557
0.7344	Intermediate Similarity	NPC91693
0.7339	Intermediate Similarity	NPC270478
0.7339	Intermediate Similarity	NPC203795
0.7333	Intermediate Similarity	NPC327106
0.7321	Intermediate Similarity	NPC32944
0.7321	Intermediate Similarity	NPC193396
0.7321	Intermediate Similarity	NPC32552
0.7317	Intermediate Similarity	NPC474271
0.7311	Intermediate Similarity	NPC477125
0.7311	Intermediate Similarity	NPC469607
0.7311	Intermediate Similarity	NPC85529
0.7311	Intermediate Similarity	NPC32006
0.7302	Intermediate Similarity	NPC476107
0.7297	Intermediate Similarity	NPC142159
0.7297	Intermediate Similarity	NPC95364
0.7295	Intermediate Similarity	NPC304180
0.7295	Intermediate Similarity	NPC179798
0.7293	Intermediate Similarity	NPC168879
0.7288	Intermediate Similarity	NPC472747
0.7288	Intermediate Similarity	NPC472750
0.7288	Intermediate Similarity	NPC320294
0.7287	Intermediate Similarity	NPC470922
0.7287	Intermediate Similarity	NPC476729
0.7281	Intermediate Similarity	NPC295347
0.7273	Intermediate Similarity	NPC228477
0.7273	Intermediate Similarity	NPC38154
0.7273	Intermediate Similarity	NPC137911
0.7266	Intermediate Similarity	NPC287236
0.7265	Intermediate Similarity	NPC471699
0.7265	Intermediate Similarity	NPC473384
0.7257	Intermediate Similarity	NPC475302
0.7241	Intermediate Similarity	NPC54843
0.7232	Intermediate Similarity	NPC469372
0.7227	Intermediate Similarity	NPC325769
0.7227	Intermediate Similarity	NPC472748
0.7227	Intermediate Similarity	NPC472756
0.7227	Intermediate Similarity	NPC476001
0.7222	Intermediate Similarity	NPC284707
0.7222	Intermediate Similarity	NPC21326
0.7213	Intermediate Similarity	NPC206595
0.7209	Intermediate Similarity	NPC67251
0.7206	Intermediate Similarity	NPC596
0.7203	Intermediate Similarity	NPC273005
0.7203	Intermediate Similarity	NPC469606
0.7203	Intermediate Similarity	NPC31058
0.72	Intermediate Similarity	NPC329869
0.7197	Intermediate Similarity	NPC221414
0.7197	Intermediate Similarity	NPC476851
0.7188	Intermediate Similarity	NPC471999
0.7188	Intermediate Similarity	NPC472000
0.7185	Intermediate Similarity	NPC262813
0.7179	Intermediate Similarity	NPC472644
0.7177	Intermediate Similarity	NPC469496
0.7177	Intermediate Similarity	NPC469463
0.7177	Intermediate Similarity	NPC469454
0.7177	Intermediate Similarity	NPC478212
0.7177	Intermediate Similarity	NPC159333
0.7177	Intermediate Similarity	NPC56448
0.7168	Intermediate Similarity	NPC261607
0.7168	Intermediate Similarity	NPC111114
0.7168	Intermediate Similarity	NPC300312
0.7167	Intermediate Similarity	NPC1679
0.7167	Intermediate Similarity	NPC472751
0.7167	Intermediate Similarity	NPC478208
0.7167	Intermediate Similarity	NPC472749
0.7155	Intermediate Similarity	NPC208094
0.7154	Intermediate Similarity	NPC474315
0.7143	Intermediate Similarity	NPC320154
0.7143	Intermediate Similarity	NPC476863
0.7143	Intermediate Similarity	NPC23046
0.7143	Intermediate Similarity	NPC475871
0.7143	Intermediate Similarity	NPC98249
0.7143	Intermediate Similarity	NPC132395
0.7143	Intermediate Similarity	NPC53396
0.7143	Intermediate Similarity	NPC469684
0.7143	Intermediate Similarity	NPC471364
0.7143	Intermediate Similarity	NPC475945
0.7143	Intermediate Similarity	NPC476862
0.7143	Intermediate Similarity	NPC471365
0.7143	Intermediate Similarity	NPC476852
0.7143	Intermediate Similarity	NPC471145
0.7143	Intermediate Similarity	NPC475873
0.7132	Intermediate Similarity	NPC243014
0.7132	Intermediate Similarity	NPC251998
0.7132	Intermediate Similarity	NPC141215
0.7132	Intermediate Similarity	NPC190065
0.7132	Intermediate Similarity	NPC471089
0.7131	Intermediate Similarity	NPC250018
0.713	Intermediate Similarity	NPC471698
0.7121	Intermediate Similarity	NPC476859
0.7119	Intermediate Similarity	NPC128733
0.7119	Intermediate Similarity	NPC474912
0.7119	Intermediate Similarity	NPC185141
0.7119	Intermediate Similarity	NPC133907
0.7119	Intermediate Similarity	NPC474742
0.7119	Intermediate Similarity	NPC46998
0.7119	Intermediate Similarity	NPC474899
0.7119	Intermediate Similarity	NPC110443
0.7119	Intermediate Similarity	NPC472753
0.7111	Intermediate Similarity	NPC242486
0.7111	Intermediate Similarity	NPC15215
0.7109	Intermediate Similarity	NPC107338
0.7109	Intermediate Similarity	NPC109607
0.7099	Intermediate Similarity	NPC181999
0.7097	Intermediate Similarity	NPC221144
0.7097	Intermediate Similarity	NPC147180
0.7097	Intermediate Similarity	NPC264634
0.7094	Intermediate Similarity	NPC35717
0.709	Intermediate Similarity	NPC102316
0.7087	Intermediate Similarity	NPC297179
0.7087	Intermediate Similarity	NPC17772
0.7083	Intermediate Similarity	NPC474741
0.7083	Intermediate Similarity	NPC309190
0.708	Intermediate Similarity	NPC469595
0.708	Intermediate Similarity	NPC140045
0.708	Intermediate Similarity	NPC295885
0.708	Intermediate Similarity	NPC220454
0.708	Intermediate Similarity	NPC212679
0.7077	Intermediate Similarity	NPC204812
0.7073	Intermediate Similarity	NPC472666
0.7073	Intermediate Similarity	NPC5103
0.7073	Intermediate Similarity	NPC99760
0.7069	Intermediate Similarity	NPC112654
0.7068	Intermediate Similarity	NPC476854
0.7063	Intermediate Similarity	NPC478216
0.7059	Intermediate Similarity	NPC474747
0.7059	Intermediate Similarity	NPC189609
0.7059	Intermediate Similarity	NPC303653
0.7059	Intermediate Similarity	NPC80781
0.7059	Intermediate Similarity	NPC149371
0.7059	Intermediate Similarity	NPC140591
0.7059	Intermediate Similarity	NPC291500
0.7059	Intermediate Similarity	NPC472754
0.7059	Intermediate Similarity	NPC197835
0.7054	Intermediate Similarity	NPC470779
0.7054	Intermediate Similarity	NPC170880
0.7049	Intermediate Similarity	NPC220155
0.7049	Intermediate Similarity	NPC322903
0.7049	Intermediate Similarity	NPC473807
0.7043	Intermediate Similarity	NPC469632
0.704	Intermediate Similarity	NPC472929
0.704	Intermediate Similarity	NPC25909
0.7034	Intermediate Similarity	NPC46761
0.7034	Intermediate Similarity	NPC476299
0.7034	Intermediate Similarity	NPC54705
0.7034	Intermediate Similarity	NPC474012
0.7031	Intermediate Similarity	NPC475775
0.7031	Intermediate Similarity	NPC476529
0.7031	Intermediate Similarity	NPC470777
0.7031	Intermediate Similarity	NPC472933
0.7027	Intermediate Similarity	NPC279859
0.7027	Intermediate Similarity	NPC38576

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 NPC245320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1249
0.2-0.3	3423
0.3-0.4	2831
0.4-0.5	1020
0.5-0.6	295
0.6-0.7	153
0.7-0.8	4
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
0.7054	Intermediate Similarity	NPD8513	Phase 3
0.6953	Remote Similarity	NPD6335	Approved
0.6953	Remote Similarity	NPD6314	Approved
0.6953	Remote Similarity	NPD6313	Approved
0.6923	Remote Similarity	NPD8516	Approved
0.6923	Remote Similarity	NPD8515	Approved
0.6923	Remote Similarity	NPD8517	Approved
0.6899	Remote Similarity	NPD7101	Approved
0.6899	Remote Similarity	NPD7100	Approved
0.6897	Remote Similarity	NPD5282	Discontinued
0.6842	Remote Similarity	NPD6101	Approved
0.6842	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5697	Approved
0.6825	Remote Similarity	NPD6882	Approved
0.6825	Remote Similarity	NPD6053	Discontinued
0.6807	Remote Similarity	NPD5696	Approved
0.6774	Remote Similarity	NPD6899	Approved
0.6774	Remote Similarity	NPD6881	Approved
0.6748	Remote Similarity	NPD6675	Approved
0.6748	Remote Similarity	NPD7128	Approved
0.6748	Remote Similarity	NPD6402	Approved
0.6748	Remote Similarity	NPD5739	Approved
0.6746	Remote Similarity	NPD6649	Approved
0.6746	Remote Similarity	NPD6650	Approved
0.6744	Remote Similarity	NPD7115	Discovery
0.6741	Remote Similarity	NPD6033	Approved
0.6724	Remote Similarity	NPD6411	Approved
0.672	Remote Similarity	NPD6372	Approved
0.672	Remote Similarity	NPD6013	Approved
0.672	Remote Similarity	NPD6373	Approved
0.672	Remote Similarity	NPD6012	Approved
0.672	Remote Similarity	NPD6014	Approved
0.6715	Remote Similarity	NPD7260	Phase 2
0.6694	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6642	Remote Similarity	NPD7492	Approved
0.664	Remote Similarity	NPD6011	Approved
0.664	Remote Similarity	NPD7320	Approved
0.6615	Remote Similarity	NPD6009	Approved
0.6614	Remote Similarity	NPD6847	Approved
0.6614	Remote Similarity	NPD6617	Approved
0.6614	Remote Similarity	NPD8130	Phase 1
0.6614	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6869	Approved
0.6593	Remote Similarity	NPD6616	Approved
0.6591	Remote Similarity	NPD6054	Approved
0.6562	Remote Similarity	NPD8297	Approved
0.656	Remote Similarity	NPD6614	Approved
0.6555	Remote Similarity	NPD5654	Approved
0.6555	Remote Similarity	NPD5695	Phase 3
0.6544	Remote Similarity	NPD7078	Approved
0.6541	Remote Similarity	NPD5983	Phase 2
0.6541	Remote Similarity	NPD6016	Approved
0.6541	Remote Similarity	NPD6015	Approved
0.6535	Remote Similarity	NPD5169	Approved
0.6508	Remote Similarity	NPD5128	Approved
0.6496	Remote Similarity	NPD7736	Approved
0.6493	Remote Similarity	NPD6370	Approved
0.6493	Remote Similarity	NPD5988	Approved
0.6484	Remote Similarity	NPD5215	Approved
0.6484	Remote Similarity	NPD5216	Approved
0.6484	Remote Similarity	NPD5217	Approved
0.6484	Remote Similarity	NPD5127	Approved
0.6479	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6336	Discontinued
0.6466	Remote Similarity	NPD6319	Approved
0.6466	Remote Similarity	NPD6059	Approved
0.6446	Remote Similarity	NPD5959	Approved
0.6446	Remote Similarity	NPD6083	Phase 2
0.6446	Remote Similarity	NPD6084	Phase 2
0.6444	Remote Similarity	NPD8328	Phase 3
0.6429	Remote Similarity	NPD6845	Suspended
0.6429	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD8293	Discontinued
0.6403	Remote Similarity	NPD5956	Approved
0.6393	Remote Similarity	NPD4225	Approved
0.6387	Remote Similarity	NPD6399	Phase 3
0.6385	Remote Similarity	NPD4632	Approved
0.6378	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5091	Approved
0.6371	Remote Similarity	NPD5211	Phase 2
0.6364	Remote Similarity	NPD7839	Suspended
0.6357	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD1694	Approved
0.6341	Remote Similarity	NPD4696	Approved
0.6341	Remote Similarity	NPD5286	Approved
0.6341	Remote Similarity	NPD5285	Approved
0.6336	Remote Similarity	NPD5167	Approved
0.6311	Remote Similarity	NPD4755	Approved
0.6303	Remote Similarity	NPD5693	Phase 1
0.6303	Remote Similarity	NPD5694	Approved
0.6303	Remote Similarity	NPD5284	Approved
0.6303	Remote Similarity	NPD5281	Approved
0.6288	Remote Similarity	NPD6274	Approved
0.6281	Remote Similarity	NPD5210	Approved
0.6281	Remote Similarity	NPD4629	Approved
0.627	Remote Similarity	NPD5141	Approved
0.626	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6686	Approved
0.625	Remote Similarity	NPD5168	Approved
0.6241	Remote Similarity	NPD6317	Approved
0.624	Remote Similarity	NPD5225	Approved
0.624	Remote Similarity	NPD5224	Approved
0.624	Remote Similarity	NPD4633	Approved
0.624	Remote Similarity	NPD5226	Approved
0.622	Remote Similarity	NPD6008	Approved
0.6218	Remote Similarity	NPD5692	Phase 3
0.6218	Remote Similarity	NPD5785	Approved
0.6216	Remote Similarity	NPD4756	Discovery
0.6214	Remote Similarity	NPD7319	Approved
0.621	Remote Similarity	NPD4700	Approved
0.619	Remote Similarity	NPD5175	Approved
0.619	Remote Similarity	NPD5174	Approved
0.6186	Remote Similarity	NPD6672	Approved
0.6186	Remote Similarity	NPD5737	Approved
0.6179	Remote Similarity	NPD7902	Approved
0.6176	Remote Similarity	NPD7503	Approved
0.6176	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7983	Approved
0.6167	Remote Similarity	NPD6050	Approved
0.616	Remote Similarity	NPD5223	Approved
0.6154	Remote Similarity	NPD5786	Approved
0.6154	Remote Similarity	NPD4634	Approved
0.6134	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD5133	Approved
0.6115	Remote Similarity	NPD7507	Approved
0.6102	Remote Similarity	NPD3573	Approved
0.6098	Remote Similarity	NPD5222	Approved
0.6098	Remote Similarity	NPD5221	Approved
0.6098	Remote Similarity	NPD4697	Phase 3
0.6098	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD46	Approved
0.6083	Remote Similarity	NPD6698	Approved
0.6083	Remote Similarity	NPD5207	Approved
0.6068	Remote Similarity	NPD5363	Approved
0.6066	Remote Similarity	NPD7748	Approved
0.6058	Remote Similarity	NPD6909	Approved
0.6058	Remote Similarity	NPD6908	Approved
0.6048	Remote Similarity	NPD5173	Approved
0.6034	Remote Similarity	NPD7154	Phase 3
0.6031	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD6371	Approved
0.6029	Remote Similarity	NPD4522	Approved
0.6017	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD4729	Approved
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD5369	Approved
0.6	Remote Similarity	NPD4730	Approved
0.5971	Remote Similarity	NPD7604	Phase 2
0.5969	Remote Similarity	NPD4768	Approved
0.5969	Remote Similarity	NPD4767	Approved
0.5954	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7640	Approved
0.5952	Remote Similarity	NPD7639	Approved
0.5948	Remote Similarity	NPD5209	Approved
0.5948	Remote Similarity	NPD6435	Approved
0.5948	Remote Similarity	NPD4270	Approved
0.5948	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD4269	Approved
0.5942	Remote Similarity	NPD8444	Approved
0.5938	Remote Similarity	NPD4754	Approved
0.5935	Remote Similarity	NPD7900	Approved
0.5935	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD6412	Phase 2
0.5913	Remote Similarity	NPD4695	Discontinued
0.5909	Remote Similarity	NPD5251	Approved
0.5909	Remote Similarity	NPD7236	Approved
0.5909	Remote Similarity	NPD5247	Approved
0.5909	Remote Similarity	NPD5248	Approved
0.5909	Remote Similarity	NPD5249	Phase 3
0.5909	Remote Similarity	NPD5250	Approved
0.5902	Remote Similarity	NPD7515	Phase 2
0.5902	Remote Similarity	NPD6079	Approved
0.5899	Remote Similarity	NPD8080	Discontinued
0.5887	Remote Similarity	NPD8451	Approved
0.5882	Remote Similarity	NPD5280	Approved
0.5882	Remote Similarity	NPD6409	Approved
0.5882	Remote Similarity	NPD7521	Approved
0.5882	Remote Similarity	NPD7334	Approved
0.5882	Remote Similarity	NPD5330	Approved
0.5882	Remote Similarity	NPD7146	Approved
0.5882	Remote Similarity	NPD3618	Phase 1
0.5882	Remote Similarity	NPD4694	Approved
0.5882	Remote Similarity	NPD6684	Approved
0.5868	Remote Similarity	NPD5328	Approved
0.5867	Remote Similarity	NPD8384	Approved
0.5857	Remote Similarity	NPD7830	Approved
0.5857	Remote Similarity	NPD7829	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