NPASS Compound

Structure

CID31641 OpenBabel06191715362D 31 34 0 0 1 0 0 0 0 0999 V2000 -4.2050 -1.3711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6665 0.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9519 -0.3619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3650 0.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8325 0.5194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0790 -2.8840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2055 -3.3886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3315 -1.9229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6664 -2.8848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0787 -1.8752 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6663 -0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9522 -1.3706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4988 -0.4813 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3318 -2.8844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4987 -1.4424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6662 -1.9234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8329 -1.4427 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8329 -1.4431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4985 -0.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6658 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6659 -1.9240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 -0.4806 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8331 -0.4810 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3645 0.0198 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -6.8259 -1.8748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6657 1.0003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6658 -2.9240 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8333 0.5190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4992 -3.3654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4987 -1.4434 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 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 14 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 9 29 1 0 0 0 0 10 1 1 6 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 6 0 0 0 12 3 1 6 0 0 0 12 25 1 0 0 0 0 13 4 1 1 0 0 0 13 30 1 0 0 0 0 14 29 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 26 2 0 0 0 0 21 27 2 0 0 0 0 21 30 1 0 0 0 0 22 5 1 6 0 0 0 22 31 1 0 0 0 0 23 28 1 1 0 0 0 23 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.14
Volume:	433.062
LogP:	3.907
LogD:	2.175
LogS:	-4.475
# Rotatable Bonds:	3
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.637
Synthetic Accessibility Score:	5.588
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:	-4.711
MDCK Permeability:	1.2082349712727591e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.898

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.895
Plasma Protein Binding (PPB):	75.92321014404297%
Volume Distribution (VD):	1.989
Pgp-substrate:	16.25547981262207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.838
CYP1A2-substrate:	0.644
CYP2C19-inhibitor:	0.352
CYP2C19-substrate:	0.791
CYP2C9-inhibitor:	0.255
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.266
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.678

ADMET: Excretion

Clearance (CL):	2.762
Half-life (T1/2):	0.184

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.828
Maximum Recommended Daily Dose:	0.407
Skin Sensitization:	0.901
Carcinogencity:	0.398
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC31641

Natural Product ID:	NPC31641
*Common Name:**	Chaetomugilin A
IUPAC Name:	n.a.
Synonyms:	Chaetomugilin A
Standard InCHIKey:	LNHWUFUMZSBRBY-YELMBXGASA-N
Standard InCHI:	InChI=1S/C23H27ClO7/c1-10(12(3)25)6-7-14-8-15-16(9-29-14)17-18-21(27)30-13(4)11(2)23(18,28)31-22(17,5)20(26)19(15)24/h6-13,17-18,25,28H,1-5H3/b7-6+/t10-,11-,12-,13-,17-,18+,22+,23-/m1/s1
SMILES:	C[C@H](/C=C/C1=CC2=C(C(=O)[C@]3(C)[C@H](C2=CO1)[C@H]1C(=O)O[C@H](C)[C@@H](C)[C@@]1(O)O3)Cl)[C@@H](C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494746
PubChem CID:	24857881
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	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	Activity	=	78.3	%	PMID[469585]
NPT176	Organism	Artemia salina	Artemia salina	Activity	=	78.3	%	PMID[469586]

☑ 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 NPC31641 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	214
0.1-0.2	1143
0.2-0.3	3940
0.3-0.4	8587
0.4-0.5	14763
0.5-0.6	9582
0.6-0.7	4173
0.7-0.8	284
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	NPC245320
0.982	High Similarity	NPC473145
0.9643	High Similarity	NPC476815
0.955	High Similarity	NPC243298
0.8636	High Similarity	NPC297281
0.8636	High Similarity	NPC473144
0.8393	Intermediate Similarity	NPC272528
0.8304	Intermediate Similarity	NPC271059
0.8304	Intermediate Similarity	NPC25666
0.8198	Intermediate Similarity	NPC215253
0.8198	Intermediate Similarity	NPC185253
0.8108	Intermediate Similarity	NPC166770
0.8103	Intermediate Similarity	NPC23497
0.8087	Intermediate Similarity	NPC199107
0.8087	Intermediate Similarity	NPC232969
0.8018	Intermediate Similarity	NPC134083
0.7965	Intermediate Similarity	NPC469851
0.7845	Intermediate Similarity	NPC469852
0.7838	Intermediate Similarity	NPC31021
0.7833	Intermediate Similarity	NPC326264
0.7807	Intermediate Similarity	NPC469657
0.7807	Intermediate Similarity	NPC244456
0.7807	Intermediate Similarity	NPC224172
0.7778	Intermediate Similarity	NPC469853
0.7686	Intermediate Similarity	NPC321496
0.7603	Intermediate Similarity	NPC66108
0.7589	Intermediate Similarity	NPC143210
0.7522	Intermediate Similarity	NPC12727
0.752	Intermediate Similarity	NPC268958
0.7519	Intermediate Similarity	NPC476008
0.75	Intermediate Similarity	NPC220705
0.75	Intermediate Similarity	NPC24651
0.748	Intermediate Similarity	NPC312833
0.7442	Intermediate Similarity	NPC477745
0.7438	Intermediate Similarity	NPC478209
0.7436	Intermediate Similarity	NPC235369
0.7422	Intermediate Similarity	NPC18945
0.7422	Intermediate Similarity	NPC105926
0.7422	Intermediate Similarity	NPC91693
0.7422	Intermediate Similarity	NPC265557
0.7417	Intermediate Similarity	NPC327106
0.7411	Intermediate Similarity	NPC166110
0.7411	Intermediate Similarity	NPC32552
0.7398	Intermediate Similarity	NPC474271
0.7395	Intermediate Similarity	NPC469607
0.7395	Intermediate Similarity	NPC472645
0.7381	Intermediate Similarity	NPC158963
0.7373	Intermediate Similarity	NPC320294
0.7373	Intermediate Similarity	NPC472747
0.7373	Intermediate Similarity	NPC472750
0.7368	Intermediate Similarity	NPC168879
0.7364	Intermediate Similarity	NPC476729
0.7364	Intermediate Similarity	NPC470922
0.7355	Intermediate Similarity	NPC38154
0.7355	Intermediate Similarity	NPC228477
0.7355	Intermediate Similarity	NPC137911
0.735	Intermediate Similarity	NPC472643
0.7345	Intermediate Similarity	NPC475302
0.7345	Intermediate Similarity	NPC248193
0.7344	Intermediate Similarity	NPC287236
0.7321	Intermediate Similarity	NPC224270
0.7311	Intermediate Similarity	NPC472748
0.7311	Intermediate Similarity	NPC474898
0.7311	Intermediate Similarity	NPC472756
0.7304	Intermediate Similarity	NPC318082
0.7302	Intermediate Similarity	NPC284707
0.7302	Intermediate Similarity	NPC21326
0.7295	Intermediate Similarity	NPC89408
0.7295	Intermediate Similarity	NPC206595
0.7288	Intermediate Similarity	NPC31058
0.7288	Intermediate Similarity	NPC469606
0.7288	Intermediate Similarity	NPC273005
0.7287	Intermediate Similarity	NPC67251
0.728	Intermediate Similarity	NPC270478
0.7279	Intermediate Similarity	NPC596
0.7273	Intermediate Similarity	NPC221414
0.7273	Intermediate Similarity	NPC203795
0.7273	Intermediate Similarity	NPC476851
0.7266	Intermediate Similarity	NPC472000
0.7266	Intermediate Similarity	NPC471999
0.7265	Intermediate Similarity	NPC472644
0.7259	Intermediate Similarity	NPC262813
0.7258	Intermediate Similarity	NPC478212
0.7258	Intermediate Similarity	NPC469463
0.7258	Intermediate Similarity	NPC469496
0.7258	Intermediate Similarity	NPC469454
0.7257	Intermediate Similarity	NPC193396
0.7257	Intermediate Similarity	NPC32944
0.725	Intermediate Similarity	NPC85529
0.725	Intermediate Similarity	NPC477125
0.725	Intermediate Similarity	NPC32006
0.725	Intermediate Similarity	NPC472751
0.725	Intermediate Similarity	NPC472749
0.725	Intermediate Similarity	NPC478208
0.7244	Intermediate Similarity	NPC476107
0.7241	Intermediate Similarity	NPC208094
0.7236	Intermediate Similarity	NPC474315
0.7236	Intermediate Similarity	NPC304180
0.7236	Intermediate Similarity	NPC179798
0.7232	Intermediate Similarity	NPC142159
0.7232	Intermediate Similarity	NPC95364
0.7227	Intermediate Similarity	NPC475945
0.7227	Intermediate Similarity	NPC475871
0.7222	Intermediate Similarity	NPC98249
0.7222	Intermediate Similarity	NPC53396
0.7222	Intermediate Similarity	NPC469684
0.7218	Intermediate Similarity	NPC476862
0.7218	Intermediate Similarity	NPC476863
0.7218	Intermediate Similarity	NPC476852
0.7217	Intermediate Similarity	NPC295347
0.7206	Intermediate Similarity	NPC190065
0.7206	Intermediate Similarity	NPC471089
0.7206	Intermediate Similarity	NPC251998
0.7206	Intermediate Similarity	NPC141215
0.7206	Intermediate Similarity	NPC243014
0.7203	Intermediate Similarity	NPC185141
0.7203	Intermediate Similarity	NPC110443
0.7203	Intermediate Similarity	NPC128733
0.7203	Intermediate Similarity	NPC46998
0.7203	Intermediate Similarity	NPC472753
0.7203	Intermediate Similarity	NPC133907
0.7203	Intermediate Similarity	NPC471699
0.7203	Intermediate Similarity	NPC473384
0.7197	Intermediate Similarity	NPC476859
0.7188	Intermediate Similarity	NPC109607
0.7188	Intermediate Similarity	NPC107338
0.7185	Intermediate Similarity	NPC242486
0.7185	Intermediate Similarity	NPC15215
0.7179	Intermediate Similarity	NPC35717
0.7179	Intermediate Similarity	NPC54843
0.7177	Intermediate Similarity	NPC221144
0.7168	Intermediate Similarity	NPC469372
0.7167	Intermediate Similarity	NPC476001
0.7167	Intermediate Similarity	NPC309190
0.7167	Intermediate Similarity	NPC325769
0.7165	Intermediate Similarity	NPC297179
0.7165	Intermediate Similarity	NPC17772
0.7164	Intermediate Similarity	NPC102316
0.7154	Intermediate Similarity	NPC5103
0.7153	Intermediate Similarity	NPC140045
0.7153	Intermediate Similarity	NPC295885
0.7143	Intermediate Similarity	NPC197835
0.7143	Intermediate Similarity	NPC472754
0.7143	Intermediate Similarity	NPC140591
0.7143	Intermediate Similarity	NPC474747
0.7143	Intermediate Similarity	NPC291500
0.7143	Intermediate Similarity	NPC189609
0.7143	Intermediate Similarity	NPC478216
0.7143	Intermediate Similarity	NPC476854
0.7143	Intermediate Similarity	NPC329869
0.7143	Intermediate Similarity	NPC303653
0.7132	Intermediate Similarity	NPC470779
0.7132	Intermediate Similarity	NPC170880
0.7131	Intermediate Similarity	NPC322903
0.7131	Intermediate Similarity	NPC220155
0.7131	Intermediate Similarity	NPC473807
0.713	Intermediate Similarity	NPC469632
0.712	Intermediate Similarity	NPC159333
0.712	Intermediate Similarity	NPC472929
0.712	Intermediate Similarity	NPC25909
0.712	Intermediate Similarity	NPC56448
0.7119	Intermediate Similarity	NPC476299
0.7119	Intermediate Similarity	NPC474012
0.7109	Intermediate Similarity	NPC470777
0.7109	Intermediate Similarity	NPC472933
0.7109	Intermediate Similarity	NPC475775
0.7109	Intermediate Similarity	NPC476529
0.7107	Intermediate Similarity	NPC478052
0.7107	Intermediate Similarity	NPC266570
0.7107	Intermediate Similarity	NPC1679
0.7105	Intermediate Similarity	NPC261607
0.7105	Intermediate Similarity	NPC300312
0.7105	Intermediate Similarity	NPC111114
0.7097	Intermediate Similarity	NPC34315
0.7094	Intermediate Similarity	NPC478233
0.7094	Intermediate Similarity	NPC69385
0.7094	Intermediate Similarity	NPC53844
0.709	Intermediate Similarity	NPC476855
0.709	Intermediate Similarity	NPC213634
0.7087	Intermediate Similarity	NPC23046
0.7087	Intermediate Similarity	NPC471145
0.7087	Intermediate Similarity	NPC478204
0.7087	Intermediate Similarity	NPC472934
0.7087	Intermediate Similarity	NPC239273
0.7087	Intermediate Similarity	NPC243065
0.7083	Intermediate Similarity	NPC471364
0.7083	Intermediate Similarity	NPC132395
0.7083	Intermediate Similarity	NPC471365
0.7083	Intermediate Similarity	NPC475873
0.7083	Intermediate Similarity	NPC320154
0.7073	Intermediate Similarity	NPC250018
0.7073	Intermediate Similarity	NPC478210
0.7069	Intermediate Similarity	NPC471698
0.7063	Intermediate Similarity	NPC261330
0.7063	Intermediate Similarity	NPC299849
0.7059	Intermediate Similarity	NPC182266
0.7059	Intermediate Similarity	NPC474742
0.7059	Intermediate Similarity	NPC471137
0.7059	Intermediate Similarity	NPC476270
0.7059	Intermediate Similarity	NPC223356

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 NPC31641 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1240
0.2-0.3	3425
0.3-0.4	2847
0.4-0.5	992
0.5-0.6	311
0.6-0.7	150
0.7-0.8	5
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
0.7132	Intermediate Similarity	NPD8513	Phase 3
0.7031	Intermediate Similarity	NPD6314	Approved
0.7031	Intermediate Similarity	NPD6313	Approved
0.7031	Intermediate Similarity	NPD6335	Approved
0.7	Intermediate Similarity	NPD8516	Approved
0.7	Intermediate Similarity	NPD8515	Approved
0.7	Intermediate Similarity	NPD8517	Approved
0.6977	Remote Similarity	NPD7100	Approved
0.6977	Remote Similarity	NPD7101	Approved
0.693	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6101	Approved
0.6923	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5697	Approved
0.6905	Remote Similarity	NPD6882	Approved
0.6905	Remote Similarity	NPD6053	Discontinued
0.6855	Remote Similarity	NPD6881	Approved
0.6855	Remote Similarity	NPD6899	Approved
0.6838	Remote Similarity	NPD5282	Discontinued
0.6829	Remote Similarity	NPD6675	Approved
0.6829	Remote Similarity	NPD7128	Approved
0.6829	Remote Similarity	NPD5739	Approved
0.6829	Remote Similarity	NPD6402	Approved
0.6825	Remote Similarity	NPD6650	Approved
0.6825	Remote Similarity	NPD6649	Approved
0.6822	Remote Similarity	NPD7115	Discovery
0.6815	Remote Similarity	NPD6033	Approved
0.681	Remote Similarity	NPD6411	Approved
0.68	Remote Similarity	NPD6012	Approved
0.68	Remote Similarity	NPD6373	Approved
0.68	Remote Similarity	NPD6014	Approved
0.68	Remote Similarity	NPD6013	Approved
0.68	Remote Similarity	NPD6372	Approved
0.6774	Remote Similarity	NPD5701	Approved
0.6752	Remote Similarity	NPD5778	Approved
0.6752	Remote Similarity	NPD5779	Approved
0.675	Remote Similarity	NPD5696	Approved
0.6746	Remote Similarity	NPD6883	Approved
0.6746	Remote Similarity	NPD7290	Approved
0.6746	Remote Similarity	NPD7102	Approved
0.6744	Remote Similarity	NPD6868	Approved
0.6741	Remote Similarity	NPD8074	Phase 3
0.672	Remote Similarity	NPD6011	Approved
0.672	Remote Similarity	NPD7320	Approved
0.6716	Remote Similarity	NPD7492	Approved
0.6693	Remote Similarity	NPD6847	Approved
0.6693	Remote Similarity	NPD6617	Approved
0.6693	Remote Similarity	NPD6869	Approved
0.6693	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD8130	Phase 1
0.6692	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD6054	Approved
0.6641	Remote Similarity	NPD8297	Approved
0.6618	Remote Similarity	NPD7078	Approved
0.6617	Remote Similarity	NPD6015	Approved
0.6617	Remote Similarity	NPD5983	Phase 2
0.6617	Remote Similarity	NPD6016	Approved
0.6614	Remote Similarity	NPD5169	Approved
0.6587	Remote Similarity	NPD5128	Approved
0.6569	Remote Similarity	NPD7736	Approved
0.6567	Remote Similarity	NPD6370	Approved
0.6567	Remote Similarity	NPD5988	Approved
0.6562	Remote Similarity	NPD5216	Approved
0.6562	Remote Similarity	NPD5215	Approved
0.6562	Remote Similarity	NPD5217	Approved
0.6562	Remote Similarity	NPD5127	Approved
0.6549	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD6336	Discontinued
0.6541	Remote Similarity	NPD6059	Approved
0.6541	Remote Similarity	NPD6319	Approved
0.6529	Remote Similarity	NPD6084	Phase 2
0.6529	Remote Similarity	NPD6083	Phase 2
0.6519	Remote Similarity	NPD8328	Phase 3
0.6508	Remote Similarity	NPD6614	Approved
0.65	Remote Similarity	NPD5695	Phase 3
0.65	Remote Similarity	NPD5654	Approved
0.6496	Remote Similarity	NPD8293	Discontinued
0.6475	Remote Similarity	NPD4225	Approved
0.6475	Remote Similarity	NPD5956	Approved
0.6462	Remote Similarity	NPD4632	Approved
0.6457	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5211	Phase 2
0.6446	Remote Similarity	NPD7839	Suspended
0.6434	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5286	Approved
0.6423	Remote Similarity	NPD5285	Approved
0.6423	Remote Similarity	NPD4696	Approved
0.6412	Remote Similarity	NPD5167	Approved
0.6393	Remote Similarity	NPD4755	Approved
0.6393	Remote Similarity	NPD5959	Approved
0.6383	Remote Similarity	NPD6845	Suspended
0.6378	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5210	Approved
0.6364	Remote Similarity	NPD6274	Approved
0.6364	Remote Similarity	NPD4629	Approved
0.6349	Remote Similarity	NPD5141	Approved
0.6341	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6399	Phase 3
0.6328	Remote Similarity	NPD6686	Approved
0.6328	Remote Similarity	NPD5168	Approved
0.632	Remote Similarity	NPD5226	Approved
0.632	Remote Similarity	NPD5091	Approved
0.632	Remote Similarity	NPD4633	Approved
0.632	Remote Similarity	NPD5224	Approved
0.632	Remote Similarity	NPD5225	Approved
0.6316	Remote Similarity	NPD6317	Approved
0.6303	Remote Similarity	NPD5785	Approved
0.6293	Remote Similarity	NPD1694	Approved
0.629	Remote Similarity	NPD4700	Approved
0.6286	Remote Similarity	NPD7319	Approved
0.627	Remote Similarity	NPD5174	Approved
0.627	Remote Similarity	NPD5175	Approved
0.625	Remote Similarity	NPD5281	Approved
0.625	Remote Similarity	NPD7983	Approved
0.625	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD5694	Approved
0.625	Remote Similarity	NPD5284	Approved
0.625	Remote Similarity	NPD7503	Approved
0.624	Remote Similarity	NPD5223	Approved
0.6239	Remote Similarity	NPD5786	Approved
0.6231	Remote Similarity	NPD4634	Approved
0.6194	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD7507	Approved
0.6179	Remote Similarity	NPD5221	Approved
0.6179	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5222	Approved
0.6179	Remote Similarity	NPD4697	Phase 3
0.6172	Remote Similarity	NPD6008	Approved
0.6167	Remote Similarity	NPD6698	Approved
0.6167	Remote Similarity	NPD46	Approved
0.6167	Remote Similarity	NPD5692	Phase 3
0.6161	Remote Similarity	NPD4756	Discovery
0.6154	Remote Similarity	NPD5363	Approved
0.6134	Remote Similarity	NPD5737	Approved
0.6134	Remote Similarity	NPD6672	Approved
0.6131	Remote Similarity	NPD6909	Approved
0.6131	Remote Similarity	NPD6908	Approved
0.6129	Remote Similarity	NPD5173	Approved
0.6129	Remote Similarity	NPD7902	Approved
0.6121	Remote Similarity	NPD7154	Phase 3
0.6116	Remote Similarity	NPD6050	Approved
0.6107	Remote Similarity	NPD6371	Approved
0.6103	Remote Similarity	NPD4522	Approved
0.6102	Remote Similarity	NPD5279	Phase 3
0.6087	Remote Similarity	NPD5369	Approved
0.6083	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD4753	Phase 2
0.608	Remote Similarity	NPD7638	Approved
0.6077	Remote Similarity	NPD4730	Approved
0.6077	Remote Similarity	NPD4729	Approved
0.6066	Remote Similarity	NPD5133	Approved
0.605	Remote Similarity	NPD3573	Approved
0.6047	Remote Similarity	NPD4768	Approved
0.6047	Remote Similarity	NPD4767	Approved
0.6043	Remote Similarity	NPD7604	Phase 2
0.6034	Remote Similarity	NPD4270	Approved
0.6034	Remote Similarity	NPD4269	Approved
0.6034	Remote Similarity	NPD6435	Approved
0.6033	Remote Similarity	NPD5207	Approved
0.6032	Remote Similarity	NPD7640	Approved
0.6032	Remote Similarity	NPD7639	Approved
0.6031	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD4754	Approved
0.6016	Remote Similarity	NPD7748	Approved
0.6014	Remote Similarity	NPD8444	Approved
0.6	Remote Similarity	NPD6412	Phase 2
0.5985	Remote Similarity	NPD5251	Approved
0.5985	Remote Similarity	NPD5247	Approved
0.5985	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD5248	Approved
0.5985	Remote Similarity	NPD5250	Approved
0.5985	Remote Similarity	NPD5249	Phase 3
0.5984	Remote Similarity	NPD6079	Approved
0.5984	Remote Similarity	NPD7515	Phase 2
0.5974	Remote Similarity	NPD7236	Approved
0.5971	Remote Similarity	NPD8080	Discontinued
0.5966	Remote Similarity	NPD3618	Phase 1
0.5957	Remote Similarity	NPD8451	Approved
0.595	Remote Similarity	NPD6904	Approved
0.595	Remote Similarity	NPD5328	Approved
0.595	Remote Similarity	NPD6673	Approved
0.595	Remote Similarity	NPD6080	Approved
0.5933	Remote Similarity	NPD8384	Approved
0.5932	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7829	Approved
0.5929	Remote Similarity	NPD7830	Approved
0.5915	Remote Similarity	NPD8448	Approved
0.5903	Remote Similarity	NPD8391	Approved
0.5903	Remote Similarity	NPD8392	Approved
0.5903	Remote Similarity	NPD8390	Approved
0.5902	Remote Similarity	NPD7838	Discovery
0.5899	Remote Similarity	NPD6921	Approved
0.5897	Remote Similarity	NPD5209	Approved
0.5897	Remote Similarity	NPD3667	Approved
0.5897	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD7900	Approved
0.5882	Remote Similarity	NPD1696	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data